Original subtitles

Once upon a time in a magical kingdom known as New York City,

in a city that doesn't sleep, but sleeps around a lot,

a land of dollar pizza and crowded subways,

there lived two millennials cursed with the paradox of choice.

Like many stories, ours begins on a phone screen

on the latest dating app called Meet Cute.

She was Wendy Brinkley, a name derived from the character

who dated the boy who never grew up.

Wendy scoured her albums for a photo that didn't include necks...

and cautiously accepted her new destiny.

Then there was Milo Marks and his 77 unread text messages.

To Milo, Meet Cute was just another app for his dedicated folder.

Milo was a 5'8"...

10?

5'8", born-and-raised New Yorker

who had no shortage of selfies that he justified as self-love.

The app asked you a few questions, then wrote your own personal love story.

Last Heartbreak? This morning. The BedfordL train. Ugh!

Romantically, Milo knew what he wanted,

as did Wendy, but she was too afraid to admit it.

They had nothing in common,

except an idealized version of modern romance.

With their profiles set, they swiped left, they swiped right.

But one day, thanks to some magic and an algorithm,

they had their Meet Cute.

They met at a cute little spot in the West Village called Lylis.

Milo found it on the Infatuation's list

of best bars where you won't run into an ex.

- He never came back from London. - He never came back?

Never came back.

Does he still have your nudes, by any chance?

Are you afraid of him leaking your nudes? Sorry, that was a weird question.

If he ever did, I have nudes of him that are not as favorable.

Really? He has peasant nudes.

- What is your baggage? - I just don't have any.

Yeah, I checked my baggage.

- No baggage, no nudes? - Just got my MacBook in a tote bag.

- Might get some work done on this flight. - What does it feel like to be so perfect?

Basically, what I tell people is like I'm just like you, except perfect.

Oh, my God. Thank you so much for getting a drink with me.

I don't even know how I made it through my life until this moment.

But, no, honestly, I think whenever I meet someone,

I create this fantasy version of this person.

And then the more that we get to know each other,

the more that fantasy just sort of whittles away,

and then all that's left is, like, this real person.

And a lot of the time, I don't like the real person

as much as I like the fantasy person.

Sounds like you idealize and then devalue.

It's a very clinical language.

- Spot-on. - Thank you.

- I'm gonna go to the bathroom, okay? - Wait, wait, wait.

Do you actually have to go or do you just wanna check your phone?

If you just wanna check your phone, we could do a mutual check right now.

- I would love to just check my phone. - Okay, okay, me too.

I could use a hit.

No notifications.

Cheers to being single.

What? Sorry.

It's okay. I like a woman who ignores me.

Only in New York could you make out in front of a bunch of garbage

and it's still romantic.

They kissed under the stars.

And after a perfectly crafted follow-up text from Milo

and an equally witty response from Wendy,

they would go weeks before they ever spoke again.

Three weeks and no signs of un-ghosting later,

Milo and his friend opted to drink overpriced cocktails

to celebrate someone from college's best friend from high school's birthday.

Did you hear about this In-N-Out Burger

that they found at a bus stop in Jamaica, Queens?

How did a cheeseburger fly 3,000 miles?

Yeah, that's fake. That's a viral stunt.

- That's not real. - You serious?

This is Hank Kadner, Milo's best and most put-together friend.

He is a financial analyst at JP Morgan

who is as savvy with his spreadsheets as he is with his dating advice.

- People will do anything for clout. - No, it's not fake.

- It was a pristine In-N-Out Burger. - Who's that?

- No. - Yeah.

- Don't. - That's it.

I'm going to marry that woman.

- You know, you always do this. - Do what?

You point at a girl and you say, "I'm gonna marry her."

In the off chance you guys do get married you're gonna say that at your wedding.

You look crazy. Look, this is how you look.

"I'm gonna marry her."

- That's not what I sound like. - That is exactly what you sound like.

- That's not what I sound like at all. - Hi.

Can I help you?

- No... - That's you.

- Why did you point at me? - I was making a point.

My friend here, he likes to... He does this thing where he...

He points at the prettiest girl at the bar and he says, "I'm gonna marry her."

And in the off chance that he happens to actually get married to that girl,

then he can say it at the reception and it can be like a cute moment.

He does it in every bar we go to.

- So it's kind of... - Okay.

So you think I'm the cutest girl at this bar?

I think that... That's pretty fair to say.

Ap spritzes on me.

- Go talk to her. - That'd be weird.

- I'm not just gonna go talk to her. - Yeah, go.

- What would I say? - Are you shy?

"I'm shy. I'm shy."

That's me being shy. How annoying is that?

We don't have time for that. Go talk to that girl!

You said you're gonna marry her. Now you won't even talk to her?

Here's what you do you. You go over, say "hi."

- Touch her shoulder a little bit. - Okay.

And then lean in, say something funny.

Maybe say it quietly so she has to, like, lean in towards you.

I had an ex who I thought I was interesting for years.

Turns out he just spoke really quiet.

That's cool.

All right, I'll leave you to it.

- What's up? Hey. - Hi.

- How you doing? I'm Milo. - Hi.

- Olivia. - Olivia.

- Nice to meet you. - Nice to meet you.

- Where are you from? - I'm from Texas.

A Southern belle.

- Yeah, there we go. - You're in the big city.

- Thank you, sir. - You're welcome, ma'am.

Oh, my God, we're doing accents. Help! No, just kidding.

No, I went to college with a friend of Lucy's who's also named Olivia.

Which is fun. And... what?

Do you dress up or you're like, "I don't do costumes."

I don't really... yeah.

- Do costumes? - I like to wear, like, a fun hat.

- Just like a normal outfit, fun hat. - I have a face for hats.

It's so round. Look how round it is.

Just thought I'd come, be a little, you know, wingman.

- A wingman. - Yeah.

That's fun, interesting. I like what you did there.

One little wing, yeah. Other wing holding him up.

Yeah, he has really bad social anxiety, so...

- I try to help him out with that. - Okay, that's intense.

- Touch it. Touch it. - Can I?

I'm giving you permish.

- It's soft, right? You like that? - Yeah, it's very soft.

- Get the aromatics. - Breathe it in.

- Let the wine breathe. - Wow, look at you go.

- Stop... look at our friends. - Look at them over there.

- You are dying to kiss my little mouth. - Maybe I am.

I don't have a top lip, but I'm... I can make it work.

- What do you mean? - I don't have a really big top lip.

That might be the best wine I've ever tasted. Where did you get this?

It's my boyfriend's family, actually... My boyfriend's family.

My boyfriend's...

family actually owns the vineyard

that this is from, and it's a rosé white wine.

- What happened? - Did you get her number, brah?

No. She actually has a boyfriend.

- How'd you find that out? - I think I knew that.

Oh, my... thanks for telling me.

Cheers for telling me that she had a boyfriend.

Drama queen.

- Or king. - Progressive.

I don't wanna put you in a box.

Yeah, drama king, or drama prince over here.

Okay, stop stealing my thunder.

People should have to wear these shirts that say "I'm single."

Because then it would help us, know who's single, who's not single.

So, you found out she had a boyfriend, then you just walked away?

Yeah.

- Serious? - The conversation was done.

- Hi. - Oh, my God!

- How are you doin'? - Liv, how are you, babe?

- I'm good. - Good to see you.

So you'll never guess what this guy just did to me.

He walked away because I said I had a boyfriend.

Yes. Yes, I did.

Why would you do that? We were having a conversation.

We can be friends.

I don't know if you guys have heard of this word before... friends.

- Absolutely. - I've heard of that too.

I think that's a very normal thing to do is to make friends.

Theoretically, yes, we can be friends,

but we're in our 20s... I'm sure you have your friends,

I have my friends, I don't really need more friends.

I sort of need something a little bit more serious.

- You're looking for a girlfriend? - Not like a girlfriend, girlfriend...

Raise your hand if you're looking for a girlfriend.

We missed it.

- That girl Jessie was cute. - Yeah, she was really cute.

- You guys seemed to hit it off. - Yeah.

- She gave me her number. - Really?

Are you gonna text her?

- I think I'm gonna call her. - What?

- Yeah. - You're joking.

No. What are you doing?

- You're joking. Hang up. - What?

- What are you doing? - It's her voicemail.

That's worse. That is so much worse.

Hi, Jessie. Yeah, this is... this is Hank.

- Don't hang up, press one. - We met tonight at Jessie's party.

- Press one, press one. - Not Jessie's party.

We met tonight at that party. You told me to give you a call.

- Erase it. Pretend it was a butt dial. - So, here I am.

So let me know if you'd like to hang out...

- Do not hang up. - And get a drink sometime.

- Okay. Bye. - Press one, then three.

What's wrong with you?

- What's wrong with you? - Let me make a phone call.

You just met and you just left a voicemail on this person's phone.

Yeah, I mean business.

- Is that okay? - No, that's psychotic!

8I would not do that, personally. That's not my ministry.

I wouldn't personally do that, but go ahead.

It's not your ministry? Who are you, Joel Osteen?

Leaving someone a voicemail... That's not your ministry?

Lead with your heart. Embrace the signs in fron of you.

Acknowledge, Compliment, Terminate, Thank

NYC NO GHOSTING DEPT.

Do you ever feel like New York is talking to you?

No.

Days later, in a different part of Manhattan,

Wendy and Jessie took New York's most reliable mode of transportation

and floated the idea of never having to be an ex again.

- Look into my beautiful green eyes. - Okay.

When someone says they wanna date themself, there's always an ex, okay?

Jessie Katz has been Wendy's best friend

since they met at Wesleyan and both got dumped the day before graduation.

They were bound by their singlehood and love of New York.

Sometimes it's us, sometimes it's them,

but behind every disappearing person, there's an ex.

- Trust me. - No, I hate that. I don't like exes.

I don't like being an ex,

I don't like talking about exes, and it stresses me out.

When someone brings up their ex, they're just tryin' to show you

that they were once a hot commodity.

So I should like them even more, because they have a series of exes.

Speaking of people you like, what is going on with...

It was at this point that the nosy app Meet Cute

reminded Wendy of her date with Milo

and gave her an idea of how to never be an ex again.

Just listen to us

Examine your emotions. Contractualize your love.

Meanwhile, bored and alone on the Upper West Side,

Milo is catching up on his stories.

Instagram stories.

Wait, is that Jessie?

Yo. Did you know Jessie and Wndy are friends?!

- Yes. - Weird...

Only in New York.

Until all of a sudden...

maybe: Wendy Brinkley hey.

we need to talk.

it's very important.

Unknowing of what was to come,

Milo met Wendy at a neutral diner placed equidistant along the F train.

So, what do you think?

Nope.

No, I'm not. I don't think so.

No, because I'm just gonna fall in love, I'm gonna get my heart broken,

and then you see how that could be very bad for me.

You use that word so loosely... fall in love.

You literally said you were gonna fall in love

with the girl we saw with the New Yorker bag.

- Okay, but did you see her, though? - Anyway, where were we?

- We were... - Oh, my God!

We were acknowledging the fact that we are both mutually heartbroken people

who want all the benefits of a relationship

without the miserable torture of actually being in one.

Wendy, a couple hours ago, I thought that you were ghosting me.

I was ready to cut you out of my life, forget about you, move, honestly.

Then you text me out of nowhere,

"Hey, we need to talk. It's very important."

All lowercase. You can understand how I'm freaking out, right?

I'm like, "She's pregnant. She's pregnant."

And if you are pregnant, then I'm ready.

We used, like, so many condoms, I wouldn't be worried.

- Thank God you're not pregnant. - Oh, man, I know, I know.

- Wouldn't that be terrible? - I was freaking out.

- Like, I said I was ready; I'm not ready. - Rewinding.

Do you not want consistent sex without the emotional attachment?

Okay, no, I do want consistent sex, I want that,

but I also want the emotional attachment.

Okay, how about this? We could be each other's guides, Milo, right?

Like you guide me, I guide you. I could teach you how to not be ghosted.

I look like I get ghosted?

- Yeah. - Me? No. I ghost.

I don't get ghosted.

You maybe look like you could use help not dating douche bags.

I don't think that men are as complicated as you want us to be.

You're playing chess, we're playing Xbox.

What?

You're playing chess, we're playing Nintendo 64.

Who?

You've never blown a cartridge?

I'm sitting here, I'm listening to you,

I'm thinking, and you seem like a sweet guy.

You seem like a really, really nice guy,

but I'm thinking that this is just maybe a bad idea,

'cause I'm just being selfish, I'm just being selfish.

I'm projecting my own fears, and I don't wanna take advantage of you.

You're a nice dude and, you know, it's stupid.

So, we should probably just sit here, enjoy this meal.

Okay, all right, after some non-awkward silence...

You've come to your senses. I am so glad! Okay, let's talk terms.

Lucky for you, I come up with this little gem.

This was Wendy's solution to any future heartbreaks,

because you can't get dumped if you were never in a real relationship, right?

Here's the brass tacks... basically, we don't get jealous of each other.

And for every night that I spend at your place, you spend two nights at mine.

- How is that fair? - You live with your parents.

I don't. I live with my mom and Larry.

And they travel a lot, so I'm being financially responsible.

I'm not even gonna consider signing that until you add cuddling.

- Add cuddling? - Yup.

And none of that on opposite sides of the bed stuff.

I need, boom, 75% of the night together, at least. At least.

Separation, that makes me think of divorce.

- I don't like it. - Most marriages end in divorce anyway.

No deal.

Fine! Fine, you can have cuddling.

We're gonna cuddle I'ma be big spoon

Sometimes little spoon 'Cause I like feelin' safe

You have a nice voice and we can sing later.

- You have to ad lib. - I don't know.

- Okay, go on, go on, go on. Go. - Okay, one more thing.

This is very important.

The words "I love you," in that order,

cannot be shared with one party to the other

unless they are used in a non-affectionate way.

What does this mean? Let me explain it to you.

Any example of that exemption would be if we were to impersonate someone

or if we use it in a sarcastic andor educational

andor non-truthful tone.

Does that make sense?

- Okay. - We shake.

And so, once upon a time, in New York City,

Milo and Wendy's non-love story finally began.

Everything was perfect.

This is going to end with one of you guys getting your heart broken.

No, we're not, because we're being really open

and transparent about the whole thing.

We're not playing any games.

Okay, but in the entire history of romance,

whenever two people start sleeping together, like, it gets complicated.

That's why we did the contract, so we know what we can and cannot do.

We set boundaries, so no one's heart's getting broken.

Yeah, the contract that establishes you guys as friends with benefits?

This is going to end poorly for you, my friend.

Look, it's not like we were friends, and then we started sleeping together,

and now we're reverting back to friendship.

It's like, you know, we started with sex,

and now we're turning that into a very beautiful

and respectful friendship with sex.

Here's where I think it's gonna go, okay?

Act one, inciting incident... You sign the contract.

You're laughing, laughing, laughing, having amazing sex.

Congratulations. Having the time of your life.

You start to get some inside jokes. "I'm hilarious."

That's my impression of you in this fun relationship.

Act two... fun and games.

You guys start to have the perks of a relationship

without actually having to deal with being in a relationship,

because being in a relationship is famously hell on Earth.

And then act three... One of you randomly decides

you do actually want to be in a relationship...

And then, yeah, movie's done.

I don't believe in traditional three-act structure.

Not every movie needs three acts. Some are just one honeymoon act.

It's kind of risk-free and there's ultimately...

It's just like me wearing the pants, which is kinda nice.

But does he know that?

Plus, I think she's as in love with me as I am with her, so it's gonna work out.

And the friends that I was talking about,

they got back together and were confused.

They were confused as to why they got back together.

And they were like, "We don't know how we got back together after all this time."

They were apart three years. They weren't together for three years.

They get back together, and then they're asking me like,

"What do you think it was?" I'm like, "I know what it was.

It was roll-over feelings.

Which is when you're in a relationship,

you got feelings, you got the relationship planned,

hoping it's gonna be a family plan, right?

Then you break up, but then you get back together

with those same minutes from that phone and it's like same phone.

Who this?

Amazing!

- I think I'm gonna marry her. - Because she laughed at your jokes?

I don't think her mom likes me, though.

- You met her mom? - Yeah, accidentally.

- How? - Bloomie's.

What were you doing at Bloomingdale's?

- I was getting free cologne. - You're stealing cologne now?

No, you just walk in, and then you get your free sample, and then you go.

- Anyway, I see Wendy's mom. - Wait, Wendy wasn't there?

No, but I recognize her mom from her Instagram.

- Cool. - So, I go over to say hello.

So I walk up to her and I'm like, "Oh, hello."

And then she's like, "Who are you?"

I'm like, "Oh, sorry, sorry, sorry, I'm Milo.

"I met Wendy on a dating app and we're sort of friends now.

"You're Wendy's mom, right?"

She's like, "Yeah, yeah, indeed I am. I don't know who you are."

She didn't know who I was.

So that either means that A, Wendy did tell her about me

and she doesn't like me,

so she's trying to neg me by acting like she doesn't know who I am

or Wendy didn't tell her, because she takes me as a joke.

Wait, do we care what Wendy's mom thinks?

Yes. I want Wendy to like me, so I want her mom to like me.

8Okay, never underestimate the will of a girl

to disrespect her parents' wishes, okay?

Make sure you get my T-zone. I've been told it's very oily.

Did I tell you that I broke up with Katie 7F?

What? I didn't even know that you were dating her.

You're already breaking up with her?

Katie 7F grew up on the seventh floor in apartment letter F in Milo's building.

They rediscovered each other sexually after a romantic elevator ride

wherein Milo AirDropped his phone number to her phone,

by mistake, of course.

That's a good one, yeah. Is that gonna make it to your Instagram?

- What? - Is it just gonna make it to your grid?

'Cause I'm usually in your story, which is dope,

love that, just hoping that, maybe we can make the next step, go to the grid.

What do you mean? I've posted you on Instagram before.

- No, you haven't. - Yes, I have!

That one time we were in Maine at that ice cream store, Scoop Du Jour.

We had mousse vanilla.

I remember you posted the ice cream cone

and then you tagged me in the photo of the ice cream cone.

No, your name was in the photo.

Okay, that's not my face, though, that's my Instagram handle.

Well, what do you mean?

People are gonna be like, "He made that ice cream for her."

I didn't. I was there, took the train up with you.

- Do you not get that? - Yes.

You do get that? So you know, but you're just ashamed.

No, it was on my Instagram. I don't understand the problem.

- We should break up. - Serious?

Yeah! I think we should break up.

- Actions speak louder than captions! - Please stop yelling at me!

It's really nice, because I realize the role that I play

is I'm sort of like this between-relationship doula for women.

Am I not present with you right now?

You're screaming at me in the middle of the park!

- I'm not screaming at you! - Yes, you are!

No, I was tryin' to have a conversation with you!

This is so embarrassing!

So they could go from, like, one guy,

improve themselves, and then go on to the next guy.

I'm sort of like a manic pixie dream boy in that way.

I think we need to just break up with each other.

- What? - I think it's over.

You're obsessed with Instagram, with social media.

I'm not obsessed.

You have a sick obsession with how people think about you.

What are you talking about?

It's like, "Damn, you're awesome, but Wendy, she's the one, you know?"

- Right... - Or at least I think.

- I don't know. - Yeah.

So, it's over, because she wouldn't post a picture of you two?

Yeah.

I think that she was embarrassed to have people know that we were dating.

I know.

So I had to break up with her. Had to do it.

- Don't be rude to my friend Milo. - Yeah... I don't know.

Over before it started, on to the next one,

which is the name of my dating podcast, by the way.

- The one you haven't started yet? - We're looking for guests.

I don't know if it's about dating yet.

It might just be about life, but if you wanna come on,

talk about any guys that you're dating, that you might really like.

If it is, can you talk about people who break up with you,

and then still follow you on Instagram,

and like all your photos and your pictures?

Orbiters. They're orbiting you.

- What do they do? - They're orbiting, you know, like...

Oh, my God, you're gonna poke my eye out!

- Stop, stop. I get it, I get it. - Okay.

All right, but there was this New York Times article that I sent you.

I don't read any of the articles that you send me.

You never read any of the articles that I send you?

Who has time?

You know what really does annoy me, though?

I hate it when someone posts something

and you can really tell that they're trying to get under your skin, you know?

They'll post something at a place that was special to the both of you.

And then it's like, "Who's this new person?

They just invited some new person."

And they're at Shakespeare in the Park

and they're just having a great time at Shakespeare in the Park

with some guy probably named Greg or something,

who works in finance and is a loser.

That is honestly called "targeted offensive orbiting,"

and it is a serious problem.

It's like a lighthouse in the deep, dark sea of emotion

that's tryin' to get the boat back to the dock.

It's literally someone going, "Hey, look at me.

"I'm recreating this experience that we had together

"with someone else, and I am happier doing it."

It's like a foghorn.

- It's... - Foghorning! Yes!

- Okay, that was good. - Oh, my God, okay.

I need some time.

- I'm almost ready, I'm almost ready. - Silence is boring.

- Hurry up. Are you ready? - I'm ready. What are your thoughts?

I thought that was funny, but it could be shorter.

I thought it was really long. But it was funny, though. It was funny.

Okay, okay. I am still trying to figure out what the movie's about.

Does it have to be about something? It's about a dude that turns into a dog.

I'm trying to think of what the movie's trying to say,

because that's just such a basic plot point.

A guy turning into a dog?

It's saying that, wow, isn't it crazy when someone turns into a dog?

I feel like that's what they're saying.

No, art is art because it lets us feel something. Here's my gist.

I think it's about parenthood and how it's difficult to raise a child,

because we really take advantage of the little moments

and how we need to savor life a little bit more.

That's just off the top of my head.

- I need more time to think. - That was smart.

- Thank you. - You're making me a cinephile.

- I know. - That was good.

What if we were a movie? What would our movie be?

Oh, my God, I think it would be like a slasher horror film

where Denzel Washington plays you and Margot Robbie plays me.

And we both get gutted and die together.

And then we have to solve our own murders.

And then we come alive in different universes

and solve who murdered each of us.

I like the different universe aspect of it.

- That's nice. - Yeah, and then we... exactly.

And then we, and then we...

- Stop, stop, stop! - And then we...

- Clever, but, no. - No? No hand holding?

Why? No! Do you want my social too?

- Yeah, that'd be nice. - I'll give you all my credit card numbers.

Honestly, I would love that. You pay for dinner anyway, so.

That's true.

So what about holding hands makes you uncomfortable?

That's Milo's doorman Cole.

I hear he's a really handsome and charming guy.

He's not my boyfriend, so why would he hold my han

Can you guys go on dates with other people?

- That's the whole point. - Why not?

Who pays for dinner?

- She does. - We split it.

- No. - Excuse me?

You do.

I literally have sent you, like, 50 Venmo requests,

and they're all sitting there, and I am being a gentle woman

by not reminding you that they are there.

Okay, I got one more very, very important question.

Hang on. Hi.

Sorry about that. Who are you here to see?

- 7F? What's your name? - Brian.

Brian, all right.

Okay, he's also totally lying about not telling people's business.

He was the person that told me my parents were having an affair.

- Stop! - Yeah.

- That's unreal. - I know.

I'm sorry!

It's totally unreal because I'm just messing with you.

- That didn't really happen. - Are you kidding?

Sorry about that. Where were we? Important question. Ready?

What happens when one of you catches feelings?

You mean if one of us catches feelings?

Yeah, yeah, if.

No, no, I mean when.

It's never if.

It's never, ever if. It's... it's always when.

You guys are gonna have a lot of fun...

but it's never gonna work out.

Take it from me.

Sweet and salty.

How's that?

How about the Razzle Dazzle? Does it razzle?

Does it...

Dazzle?

All right, that's it.

- No. It's not. - No. Okay.

Well, at least you're predictable.

Cookie dough. Why would you say that?

Well, you just gotta pick a flavor and then just go with that flavor.

And why would I pick a flavor and just go with that flavor

when I can try all the flavors?

Because if you try all the flavors,

then you never really get to experience just one good flavor at once.

- Let me think about that. - Yeah.

I think I'm just gonna exercise my right to try all the flavors because I can.

And I'm going to get the vanilla cone.

- Boring. Predictable. - That's not boring.

No, I like vanilla, because I'm traveled, I'm wise,

I'm cultured, I've had the other flavors.

Chocolate varies too much brand to brand.

Cotton candy, that's one of the fun flavors, right?

You take two bites of that, too sweet.

Thank you.

- It's melting and everything. - Cheers.

Okay, well, I guess you'll never experience the joy

of having a Razzle Dazzle, salted caramel,

and cookie dough, in a cup, please.

I guess you'll never experience the joy of committing to something.

What are you guys really talking about?

Just some metaphors.

Yeah, metaphors are great ways to talk about things

that you don't actually wanna talk about.

Do you wanna check out?

Three avoided "what are we" conversations later,

Milo wished he was the flavor that could make Wendy happy.

I think you make me a better person.

I'm literally the same person you've dated your entire life,

and if you're really on the quest to look for the one,

then you really have to stop looking in the same place.

I think you need to give yourself more credit.

You don't make me a better person. That's why this works so well.

We're like the TV show you watch every night,

that episode of The Office that you know line by line.

You just know what to expect.

What's wrong with that?

Okay!

Wait, wait, wait.

No, I know... Stop, I know who is in Hook.

Rufio.

- Yes, that's his na... - Has a name.

Okay, calm down.

His name is, uh...

- Three... - Two...

No, wait, no, no, no, stop!

- One. - Stop!

Chug, chug, chug, chug!

- Chug it, chug it. - That's alcohol.

No more.

- Dante Basco. - Should we split it?

- No, I think we should do individually. - Why?

- That's, like, extremely difficult... - Hank had two mains.

- He did, didn't he? - Yeah, I'm bulking.

You ate like two people. You got the sea bass and you got a hanger steak.

But that hanger steak was not for the table, that was for you.

Okay, fine, I'll... I will pay the tip.

- Okay. - Okay.

- You guys! - Settled. That's fair.

Say "Thank you, Daddy" on three. One, two, three.

- Thank you, Daddy. - Very good.

- Why didn't you say it? - 'Cause it's uncomfortable.

- I always tell them that. - He liked that too much.

Now that that's settled, Wendy has big news, speaking of news.

- Does she? - Wendy is moving to LA.

She's movin' to LA. She just told me.

- That's exciting, that's awesome. - No...

I... what?

I'm... I'm just... contemplating a life there...

Like, on purpose?

Hate that for you.

- LA is a haunted house... - Oh, my God.

Full of cardboard sunshine people.

Why did you do that? See, you've made her mad.

- You're being a child. - I'm not being a child.

You're being a child. You look like a child right now.

The way you're drinking is childlike.

If they're not a couple, they're definitely fighting like a couple.

- Well, they are. - I don't think... that was bickering.

- I don't think that was fighting. - It wasn't fighting.

You were being kind of dramatic. That wasn't fighting.

That was a discussion. We were discussing.

It was... it was a salon.

My ex just moved to LA.

- Oh, really? - I'll give you her number.

- You guys would totally get along. - Yeah.

Amazing. That sounds incredible. What's up with your ex?

Cool.

She just moved there a few months ago.

- I didn't know you still talked to her. - I don't, really.

She just told me that she was leaving to New York.

She told you? Like, you guys text?

Not often, but she texted me because we have...

a "text when a big life event happens" type of relationship.

She's moving to LA? What is she, an actress?

- She's moved to LA. - She's an actress?

- No, she works in PR. - Is she blonde?

Okay, how tall she? Look at me in the eyes.

How...

How tall is she?

You know, that's something... That we don't do that.

We don't have to do that. We're immune to stuff like that.

We don't have that element to be worried about it.

We can't even get to the point where we fight.

- I'm not mad. - You're overreacting...

I'm overreacting? It's called reacting, so.

- You know that I hate... - I've mentioned that...

Overreacting? Are you serious? I am going to go.

This was so freaking cool and fun.

- Bye. - Bye.

- Have an amazing night, everyone. - Love you.

- Love you. - Later.

You still have her number?

Yeah, what am I supp...

Am I not allowed to have an ex-girlfriend?

- You need a whole new phone now. - I'm gonna go deal with this.

- Okay. - Okay?

- Are you leaving without paying? - Leave a card.

- Definitely leave a card. - But you got a lobster, that's not even...

Even the size, what do you think?

Is there... no way.

- No kiss? No kiss? - No.

PDA is a no-no for us.

- Come on, just give me a kiss. - It's gross, it's gross.

- I don't wanna do it. - Look at them.

Are you kidding? I think they're overcompensating for something.

- They were literally just fighting. - And now they're not. I don't know.

I think they really love each other.

And I think that they've been dating for, like, two weeks.

Two months!

They don't love each other. That is the honeymoon stage.

I don't know. So? What? My place, your place?

What are we doing? What are we doin'? I think I owe you two sleepovers, so.

Actually...

- I do. - You got other plans?

Okay, all right. So what? That's a date?

Yeah. Yeah, I already got a date.

All right.

I have to dip my toes back in the water. Come on.

Actually, while I have you,

is this a good text to send someone or is it, like, way too aggressive?

- Really? - What?

Wendy, no matter what I tell you,

you're just gonna like the guy that doesn't like you back.

Emotionally unavailable people need love, too, so help.

We're more afraid of you than you are of us.

That's not helpful.

Give me something more. Elaborate, please.

Be your charming self, make small talk,

have an emotional connection, bite your lip, right?

But you can't text him. Do not! Seriously, you have to act like he died.

Do not text him, and then, boom, he's yours.

He'll fall in love with you.

Thank you. But I have to go, and I'm gonna call you later.

Yeah, thank you for the drinks.

I kind of wish you let me split it, but, whatever, it was really nice of you.

So thank you... again.

Yeah, of course, no worries. So drinks again next week.

This was Mort, a man Wendy matched with on Meet Cute.

He lived only one train stop away and was a clean 6'2".

Rather than seeing a therapist, Mort co-hosted a podcast

where he interviewed ex-girlfriends about what went wrong,

called Let's Catch Up, available on iTunes and Spotify.

So, I'll see you again for drinks next week. We'll do drinks next week.

- No, actually. - What? Why? What?

- I mean, you lied. - About?

Come on.

- What? - Mort.

- Yes? - Mort, you said you were 6'2".

I am essentially 6'2".

- What are you talking about? - You're not 6'2".

Okay, fine. I'm like 6... I'm like 6... I'm like a solid 6 foot.

I'm like a clean 6... 6'0".

Sure, you know what? You're right. If I take off my shoes, yeah, I'm six foot.

But shoes back on, I'm probably like 6'3".

"6'2" is merely a number.

You don't wanna give this a chance

'cause I'm slightly smaller than I said I was?

"Slight" is generous, Mort, but I appreciate you keeping yourself up.

Here, come take a seat, let me explain something to you.

Your optimism is endearing, honestly, but let's dig deeper.

Why do you feel the need to exaggerate certain aspects of your profile?

- I mean, do you not love you? - I do love me.

Oh, good. Let's start there.

It's just that dating... Dating can be so hard.

It is. It can be.

And I go on all these dates and I finally meet people that I like,

and then the more I like them, the less they like me.

I know the feeling. Do you smoke?

- No. - I don't either.

Listen, Mort, here's the thing.

Sometimes things in life just don't pan out the way we want them to,

but you have to be able to get over it and you have to be okay with that.

On a different couch, in a different part of Manhattan,

Milo was enjoying temporary validation

from all the likes on his most recent selfie.

He was surprised, but not shocked, to see that Katie 7F liked his photo

despite their theatrical Central Park breakup.

He quickly scrolled her grid, and with no evidence of a significant other,

her percentage of singlehood was likely high.

hi

Hi Milo.

what

are you up to?

Do you always text like a Rupi Kaur poem?

...yes?

Did you know that Sunday is the busiest day for people on dating apps?

I wonder if it's because of the impending horror of the work week.

Actually, I'm sure that's probably it, yeah.

And January sixth is the busiest day of the year.

Why is that?

'Cause people want Valentines?

No, I think it's because people break up

after they go meet each other's families,

'cause they realize, "I was just in this relationship

so I wouldn't be the only single person at Thanksgiving dinner."

And did you know that you're 80% more likely to be swiped right on

if you use the word guacamole in your profile?

Guacamole?

- Do you know what men lie about? - Their height?

- How did you know that? - Because I'm 5'8 ", not 5'11".

Right. Yes, I wish I knew that.

Do you wanna come over?

- That's a rule breaker. - What.

I am sleepy, and I'm already in bed,

and I'm watching Harry Potter, and... yeah.

But I can talk to you until I fall asleep.

Okay, I'll settle for that.

- Wait, where did you go? - I just checked Instagram.

Oh, my God.

- Thank... - But yeah, yeah, I have to go.

What? Wait, what?

Yeah, I gotta... I gotta go for real.

Whatever, you suck.

- Hi. - Hey, what's up?

Hey.

- Thanks for coming. - Yeah, for sure.

- Do I... - Good, yeah, yeah, yeah.

So, yeah.

Easy time getting here?

Yeah, I mean, all of six minutes it took me.

- I took the stairs. - Okay.

A little cardio, a little workout, that's good.

Got my steps in.

- That's good. Do you want some wine? - I would love some wine.

- Yeah, okay. - Yes, one of those days.

- I've got a nice Flemish red. - Yep.

Okay.

- You like wine? - Yeah.

You know, I indulge, I would say.

It's hard not to miss it?

- Right. Cheers. - Cheers.

Despite the contract stating they could sleep with others,

Milo had a rush of morning guilt

and Wendy couldn't help but feel a little bitter.

I guess there's something you can learn from that.

Don't be stupid, don't just immediately have sex with someone, I guess.

But like any healthy adult relationship,

the two addressed their emotions head-on.

Why are you being moody?

- I'm not. - You're being really moody.

- No, I'm not being moody. - Oh, my God, let's not play this game.

Just tell me if you're mad. If you're mad, we can talk about it.

I'm not mad, I'm not. I was just saying.

While one relationship tiptoed around their feelings,

another was about to take a huge step forward.

Okay, this neighborhood is very hot, very hot.

Did you notice the Whole Foods they were building?

They were opening one down the street.

On 24th?

- No, the one on 23rd. - How's the landlord?

Completely insane. You'd be lucky if you get your security deposit back,

but you have to ignore all these red flags for...

natural light.

It's a little small, right, Hanky?

It's New York! Yeah, can I think about it?

Well, not too long, because this place is gonna be snapped up.

A place like this in this hot neighborhood, very desirable.

Take five seconds. Five, four, three, two...

I'll take it!

- Good choice. - Are you serious?

- She's good. - Okay, let's go.

You're very good at your job. All right, let's see.

You're gonna definitely have to move some of this furniture.

It's very sad. Very, very sad couch over there.

And you're gonna wanna move that up.

You're gonna have to get rid of literally everything in here.

This is the saddest couch in the universe. That's scientific fact.

The sad Eiffel Tower, "I'm a girl who studied abroad" painting,

you'll have to move that.

- Come on. - You mean...

You mean, we're gonna have to move that.

What are you talking about?

- I know that your lease is up. - Okay.

It's coming up, and you don't like living with roommates...

I don't.

But what if you live with me and I was your roommate?

Are you askng me to move in with you?

- In front of our new friend? - Yeah.

- Are you nervous right now? - A little bit.

I know, I could tell. What do you want me to say?

- You think I'm gonna say no? - I want you to say yes.

- Of course I'll say yes! - 'Cause I like you so much.

I like you! I like you so much.

- What do you mean? Wait. - What?

- You... you like him? - Yeah.

- You like her? - Yeah.

- Big-time. - Do you love her?

Do you love him?

The first time I'm gonna say it in front of...

- He's obsessed with me. - Yeah, I love you.

- I love you too. - So beautiful!

We're gonna live in this little shit-hole together.

Okay, but first, you're gonna have to...

First and last month's rent and my commission.

You know what? Anything for you. You're a queen. Come here.

You're our girl.

- That... that's nice. - Thank you.

We live here now! That's my shitty couch!

To grab your attention with its nice, broad green leaves

and its air filtering prowess. Now give it a little touch.

- Don't... no, no, not too much. - Sorry.

Now it might require a little bit more maintenance than the other plants...

But as we all know, nothing good comes easy, right?

Do you have anything from the Jurassic era?

- You know what, let me check. - I'll look too.

- Let me see. - I'll give it a quick gander.

You guys just do your thing.

I want something that looks like it came out of a movie.

- So you want a fossil? - I would also want a fossil, but...

Is there a price tag?

What's wrong?

- We have to go now. - Why?

- I wanted to get the plant. - We have to go now.

Don't forget, don't forget...

- Hey, Bradley! - Who is...

Damn, damn... Wendy, Wendy. Okay, basically, listen, here.

SparkNotes version.

I dated that guy Bradley over there for a couple of months

and he basically ghosted me for an unknown reason.

Maybe it could have been because I texted him a bunch of times.

I'm not sure, but he's here, so we're gonna say hi.

- All right. - We're gonna be fierce.

Be the better version of you.

- Hey! - Hello!

I was blind, but now I see.

- I see you. - Missed it, missed it.

Sorry, that was aggressive.

- Hi, what's up? - Kind of insensitive, given the climate.

- Okay. - How are you?

Good. I mean, I don't know, how is the sun, you know?

How is the sky? It's grateful and expansive.

- Thank you, Father, up there. - Thank you.

Thank you for asking me. How are you?

- I'm amazing. Look, I'm... - Come here, come here.

Okay.

Yeah, it is you, it is you. Sorry, sorry, sorry.

- Brad, baby, I found one. - Erica.

This is Wendy, actually.

- Oh, hi. - Hi.

- Hi... - Hey.

She looks just like you.

- Stop, that's so... - You're so sweet.

This is Milo. Sorry, this is Milo.

- He's.. He's my friend. - Yeah, hey. What's up?

He's my sex friend.

- Yeah, by contract. - By contract, by contract.

Well, Erica's my fiancée. So, we're waiting.

Just kidding! We're freaks!

Did you hear that, Milo? He has a fiancée now.

That's crazy! It's wild!

I just... I remember you kind of saying something along the lines of

"Hey, you know, Wendy, I don't wanna date you anymore.

I wanna date myself and be single."

And I was like, "Cool, you go do that."

Well, last time you saw me, I was like... "Whoo!"

- You know? That was me! - Yes, yes.

But not anymore, not anymore, 'cause I was looking. I was searching.

But the universe provides, right?

"I was trying to date myself," you know, what an egotistical thing to say.

- No, babe, that was your past. - That was my past.

Then they put us together at the singles' table

at a mutual friend's wedding and...

I don't know how to describe it, we just fell in love.

We just fell in love. I'm so happy to say that out loud.

- It still gets me. Oh, my God. - Yeah, baby.

Isn't that great? We found the energy.

- Isn't that great? - That's great.

You know what that is? That's rollover feelings.

It's like rollover minutes, but with feelings.

It's like rollover minutes, but it's with feelings

and you got the family plan of feelings.

- Like the phone plan! - Oh, my God, oh, my God!

I'm gonna roll over with laughter from that.

You jokester. So charming. He's funny.

You're very funny. What does he do?

- It's a new bit I'm working on. - He's a comedian.

- I love Canadians. - Me too.

That's so cool. They are very funny.

I have some rollover feelings about a coffee table there.

- Yeah. Oh, my God! - I'm sorry, I stole your joke.

- Mee-lo? - Milo.

- Milo, great. Okay. - Milo.

- Bless you. - Yeah.

Good luck with the sex. It sounds fantastic.

- Bye. - Goodbye.

Blessings to you.

After running into Bradley,

Wendy was visited by Ghost of Boyfriends Past.

Always the heartbroken and never the heartbreaker, it finally clicked.

To never feel heartbreak again, she need only do one thing.

Do you want to make changes to your profile?

On a different phone screen, with no new matches,

Milo made a life-changing decision.

As both were down on dating,

Milo and Wendy visited Tompkins Square Park,

New York's breakup hot spot, to relieve some despair

via people who were full of even more resentment than they were.

"You don't take my food blogging seriously."

"I would love to take your food blogging seriously,

but you literally only blog things I'm allergic to, I can't eat."

"Yeah, I blog things that you're allergic to

"because I wanna raise awareness around your allergy."

- "Babe, I need you to stop crying." - "I'm not crying."

- "You're always crying." - "I don't always cry."

"Can we just have an adult conversation for once?"

"We're are having an adult conversation."

- "Oh, my God." - "Stop. Stop it."

"I literally can't. I need to go have a beer."

"You're just not emotionally vulnerable like I am."

"I am!"

"And that's something that you need to work on."

"I bought the journal like you told me to."

- "I bought it!" - "You never use it, 'cause I've read it."

You ever think about how now it's so easy to break up with someone?

Back in the day, what?

You had to, like, show up to their house, do it in person.

Now you can just... "It's not workin' out, slanty face."

I, for such an occasion, have a pre-written breakup text.

- Like a template? - Yeah.

- Seriously? - Yeah.

- Show me. - No.

Why?

Fine.

- You ready? - Lay it on me, yes.

- Break up with me, break my heart. - Okay.

"Hey, insert name there, thank you so much for the last couple of dates.

"They were really fun.

"Unfortunately, I feel more of a friend vibe going,

"but you're such a great person, and I really hope

"that you have a great future and a successful year."

- That's it? - That's it.

You feel more of a friend vibe going?

If I got that after a date, I'd be like, "Oh, great, they wanna see me again."

- What? - Yeah, that doesn't seem bad.

I think you're the only person that would read that text that way.

Honestly, just ghost me.

I'm not even... I don't wanna even get the text.

Just let me spiral, let me make up my own story.

- Let me write that in my Noteshelf. - Okay, I keep it in mine.

"Ghost Milo."

It's just every time I've liked someone, they've ghosted me.

And at this point, fine, I'll just be single forever.

- Are you kidding? - It's like, what am I doing?

You are smart, and funny, and kind, and inspiring,

and hard-working, and determined, and passionate.

You're gonna be just fine.

Okay.

- That was a good pep talk. - Thank you.

I think I know what I want now.

What is that?

"I think I'm gonna be a food blogger and..."

"You're gonna be a food blogger?"

"I'm gonna start by blogging about this brunch we're going to."

- "I'm all about brunch." - "It's gonna be so good."

"It's gonna be so good, right? It's gonna be so good."

- "You want a ride?" - "Okay, go."

To blogging!

- Oh, my God. - Your curls are literally perfect today.

- Can I touch one? - Yes, every curl has a story.

Does it? Tell me this one's story.

What happened to this one?

He is a first-generation college student.

And he is going to be taking care of his family.

Oh, sad.

Which is so... But he really takes pride in it.

He really takes pride and enjoys it.

- Get another one. - All right, I want this one.

- That one is a billionaire, actually. - Okay.

- All the other curls hate him. - That makes sense.

- That's makes sense. - Yeah.

Like the Daddy Warbucks. I don't know why I'm referencing musicals today.

What's going on here?

- What? - What?

You decided to sit on the same side of the booth.

It's kind of a pretty big booth.

Would... yeah, well, if we sat right there,

we'd be closing ourselves off from the world.

Exactly, I like to look. Like, "Oh, hey, what's up?"

Look, that guy... That's a great coat. Maybe I wanna get that coat.

- A taxi! - Look, there's a taxi.

We're taking in New York.

Also, the seat creases there. I don't wanna sit in the sink.

If you don't like the streets, don't live in New York.

Also, I like to look at you in the eye.

I like to have a conversation with you eye to eye.

Are you gonna pull up a chair right there and then...

Exactly! Exactly, that's so rude.

- It only makes sense. - Something's different.

You guys are more into each other than you were before.

- That... I mean, yeah. - No.

It's...

You've noticed that we have a...

- Have a freelance. - We upgraded.

We're freelancing an upgraded relationship.

Yeah, a freelance relationship.

- A free... A freelance relationship? - Funny you should ask because...

Because a freelance relationship is a relationship where you are...

Given your status, you have a fair amount of benefits.

You have a certain amount of relationship benefits.

Benefits that you can take, and you leave the awful ones.

So it's friends without benefits.

Depending on your employer and your insurance package.

It's a bit I'm working on.

- You got yours wallet-size? - I did, actually.

It's really nice. Here, I made you one too.

Thank you.

Let me see this.

And look, laminated.

You went to Staples,

and took a little piece of paper, and made them laminate it?

- Why are you so invested? - What is this? Do you litigate?

Okay, can you guys stop talking?

I called you here today because...

Yes!

Yes!

Yes, put it on, put it on!

- Okay, seriously, though, that is... - That is...

Amazing!

Yeah, I'm gonna ask her on Thanksgiving.

You wanna touch the box?

This whole relationship is moving at seventh grade speeds.

- Yeah, we're doing... - It is, kind of.

Is it messed up if...

Okay.

Do I owe this girl... Woman a breakup text if we only went on one date?

No. Maybe, honestly, if you had sex with her.

- Did you have sex with her? - No.

Well, then you don't really need to explain anything.

It's not really ghosting if there's no sex involved

or if you went on more than one date.

- Okay, I lied. We had sex, we had sex. - Then you should probably send a text.

You should send, like, a simple breakup text.

But I feel like if I do that, then she's gonna think

that it's because we had sex, but it's not.

It's because... I just didn't like her.

She just... I feel like that sounds harsh, but she...

It does.

She just wasn't it. She just, she just wasn't it.

She kept asking what time I was born, and that was the only question

she asked about my personal life at all.

The whole date. And then at the end of the night,

she was like, "Have a wonderful night,"

just like in this weird tone, like Mary Poppins tone.

And she lives in Murray Hill, so.

- Very dramatic. - That is a no.

Why don't you just be like,

"Hey, you know, date was fine, we're better as friends"?

I don't wanna see her again.

Okay, then just be like, "Hey, I'm not looking for anything serious."

Well, that'd be lying.

Okay, then just don't say anything at all.

Okay, settled. I won't say anything.

- Nailed it. - Easy.

Could you pass me a fortune cookie?

No, it is bad luck to eat a fortune cookie before you have finished your meal.

- Okay. That makes sense. - You're welcome.

Just gonna... get some dinner running.

God. So smooth.

What if we became boyfriend and girlfriend?

Yeah, what if we were boyfriend and girlfriend?

- No, I'm serious. - It's a great idea.

What if we were exclusive?

- But you don't want that. - Yeah, I do.

Wait, why are you doing this?

Because I think that we would be good together?

And I like what we're doing.

You know, we're... We have this great thing where

we're allowed to be single but not be lonely.

- Like, that's the dream. - I don't know.

I feel like we have two different versions of what a dream is.

Okay, well, then maybe we should stop.

Stop what?

Stop hanging out, stop talking every day, stop watching TV shows together.

Okay.

That's cool, but the thing is...

I love you.

I love you.

I'm sorry. You don't love me.

There's no way, you don't love me! How could you love me?

What do you mean how could I love you?

What... we spend so much time together.

- Milo, Milo, Milo, you love everyone. - We're always...

You love everyone and everything.

You're afraid.

- You're afraid. - Excuse me?

- You're afraid. - What are you even talking about?

- You're afraid to be loved. - That's not fair. I'm not afraid.

You...

So if it's going good, you like it, you're having a good time,

which is what you said, we're havin' a good time, what's stopping you?

Okay, you wanna know what happens? What happens when we date?

Let's just say we start dating, all right?

And then suddenly, there are all these expectations

and they just keep piling, and piling, and piling, and piling, and piling,

and then suddenly, I'm getting mad at you,

because you're not expressing your feelings well enough

or you don't even wanna come near me, because I'm suffocating you all the time.

And then we finally get to the point where we break up,

and we never see each other again,

and we have no friends, and we're just alone.

That wouldn't happen.

That wouldn't happen. Not to us.

- You're afraid of being alone. - I'm not afraid of being alone.

I love bein' alone. I've been alone so much.

- I just wanna be alone with you. - And I wanna be alone alone.

I haven't even thought about her in what? Three weeks.

I can't even... it's so far out of mind at this point.

That's great!

I can't get Milo out of my head.

I'm sorry, it'll pass. Remember, half the time you were together

equals the time it takes to get over them.

It's math. I'm basically a scientist.

We were supposed to be the unsinkable relationship, you know?

- Like the Titanic. - The Titanic sunk, dude.

But the love lasts forever.

I'm worried I made a mistake.

No, it didn't work out, that's okay. Just 'cause it ends

doesn't mean it wasn't a successful thing when it was happening.

Yeah, but what if I didn't give it a real shot?

- I always do this to myself. - Is this self-sabotage?

I really just hope that she found somebody that she likes.

Like, I'm good, I just hope she's good.

What? Why are you wishing... You are being way too hard on yourself, okay?

You guys weren't supposed to be "not together" together anyways.

I mean, how can you even break up when...

- You weren't even dating. - It's for the best.

I'm sure he'll just fall in love

with the next girl he locks eyes with on the I train.

- Have you spoken to each other? - Have you spoken to her?

- No. - I accidentally viewed her Linkedln.

Well, he viewed my Linkedln.

- How is he? - How is she?

- You'll see her at the wedding. - You'll see him at the wedding.

- Are you alone? - Wait, who are you talking to?

- I'm with Hank. - I'm with Jess.

- That's so cute. - Cute.

Are you seeing anyone?

I'm just sort of, like, dating myself right now.

Yeah, just... yeah, and I'm really happy about it.

Yeah, actually, this guy.

He's in finance, he works constantly,

and he's completely emotionally unavailable,

which is perfect, and I'm really happy.

That's great.

Dating sucks.

Absolutely.

Well, we can definitely be there Monday if we have to.

I would never say we won't.

Okay.

Absolutamente.

No, we're delighted.

You kidding me? This is great!

So, hey.

This was Trent Wilkinson,

an incredibly emotionally unavailable 34-year-old

who lied about his age to make the Feingold 30 Under 30 list

for selling his sock company, GotSoxx, spelt with two Xs.

He DM'd Wendy on Instagram after finding her geo tag

at Surf Lodge in Montauk.

Wendy had spent the last three weekends

at Trent's apartment in Tribeca and even had her own toothbrush.

Attention, Kmart shoppers, I'm gonna be presenting

to, like, a whole bunch of restaurant groups

because they said that my app is brilliant.

- That's amazing! - Yeah! I know.

Oh, my God! I mean, it is brilliant and you're brilliant.

- Yeah. Makes sense right? - Yeah. It does.

It makes perfect sense. When are you leaving, then?

It's, like, Sunday.

Sunday night.

Sunday, like tomorrow?

Yeah.

- Tomorrow... tomorrow night. - Awesome.

Awesome, and how long are you gonna be gone?

They said it was gonna be like meetings, and greetings, and stuff like that

for, like, a couple of weeks.

Yeah.

- That's amazing! - Yeah.

No, I know, it just... maybe we could, like...

just kinda slow her down a little bit.

Yeah, I... I know. I... yeah, I mean.

Just, like, pull the car over for a bit.

Bad metaphor. Just slow down.

While Wendy sold all her stock in Trent,

Milo was three stops into the one on his way to a John Mayer concert.

Did I tell you about the time that I got a fortune cookie?

- No fortune in the fortune cookie. - No.

Her name was Jenna Brookes,

and she was a recent graduate of NYU's Gallatin program

where she wrote her thesis

on the life, death, and rebirth of chivalry in millennial dating culture.

Yeah, there was no fortune in the fortune cookie.

- That's crazy, yeah. - That's crazy.

What's wrong?

- Nothing. No. - Something's wrong, what's wrong?

- No, I'm excited. - No, you're not.

- Yes, I am. - You're not excited, something's up.

- No. - We're going to see John Mayer.

- Yay! - You don't seem stoked.

- No, I'm excited. - Something's wrong.

Something is wrong

I'm not going to stop bothering you until you tell me what's wrong.

I think we want different things.

What? What, what do you mean? What are you talking about?

I don't think I see a future with us.

No.

You FaceTimed my mom.

- Yes, that was... - I let you FaceTime my mom.

She's wonderful. I loved her! I wish that we... I love her.

The next stop is Heartbreak Boulevard.

I think you... I like you.

You deserve someone great, so...

No, I'm sorry, I don't wanna kiss you.

Okay, don't cry. I have to... I have to go.

Things turn around, they change.

That sounds like it should be encouraging,

but it's actually really depressing.

Okay, new topic.

The podcast thing.

Did you start it? You should start it.

Yeah, I'm probably gonna do some, some episodes.

I just gotta get a microphone,

and then come up with some ideas for episodes and the podcast.

Well, here's an idea. You should have me on as a guest.

Maybe not like your first guest out of the gate,

but let me... I quit this place,

I'm gonna spill all the tea on everybody.

I mean, there's some stuff that's going on in here

that I think the listeners would wanna know.

Yeah.

Come on, man, I miss you smilin'.

You're, like, one of the few reasons why I stay in this place.

The phone never stops here...

Front desk.

At a bar in Hell's Kitchen, where she would never return,

Wendy listened to a man she met at Whole Foods

talk about his screenplay that would never get made.

Yeah, so the script's back at my place if you wanna come read it.

So this is really fun.

I'm gonna go to the bathroom first before that.

- Lovely invite, thank you. - We can go right now.

- I'm actually right around the corner. - Yeah.

I could play the lead or you could play the lead.

- It's sort of a strong female heroine. - Yep.

And, you know, we're thinking...

Hello, hello, hello. I only got about five, so let's keep 'em comin'.

Yeah, okay, so who paid for dinner?

He did, but I did offer to split, and then he insisted on doing it,

so I was like, "Whatever, this is terrible anyway."

Will you ever see him again?

I like to go into these things open-minded.

If it goes well, it goes well, but...

Look, we all know dating sucks,

but wouldn't you just rather be with Milo than keep this up?

Is this an interview or is it a therapy session?

Thank you so much, goodnight.

katie! how are you this fine sunday. wanna go see a movie or something?

Hi!

I'm actually seeing someone at the moment...

But we could ge as friends! If u want?

Do we have to go to John Mayer?

jenna! hope all is well since oursubway convo.

anyway, I know you weren't looking for aynthing serious

and neither am I, but do you wanna go grab a drink?

I miss you!

I miss you t...

So, Milo, you just got your heart broken.

How are you feeling? What's going through your mind right now?

Thanks for having me, I'm really excited to be here.

I am completely dead inside.

I feel nothing.

I feel like a no one, a nobody.

I haven't showered in a long time.

That's amazing! Everybody, give it up for this guy, he's so good.

So are you wondering why maybe the breakup happened?

Do you think it's something that you said

or maybe something that you didn't say

or are you just totally broken as a human being?

I'm sort of like a cracked iPhone screen right now.

Yeah, you could fix me,

but it's probably best to just upgrade to the next and better thing.

All right, everybody, that's all the time that we have.

Give it up again for Milo.

He's so good, he's so funny, isn't he great?

Isn't he amazing? Isn't he great?

Isn't he so good? Milo's so great, he's so good!

Isn't he great? Isn't he amazing?

Isn't he great? Isn't he amazing, isn't he so good?

Such a good catch. So funny, so good, so funny.

You're strong, you care, you're a catch, you're humble.

You're underappreciated. You're...

You're trying. You're trying, you're trying, you're...

I love New York.

The only place where you can get toilet paper,

a toothbrush, and a turkey bacon sandwich all in one place.

This is a decent one,

but I really like a "bougdega" instead of just a plain bodega.

- You know what I'm sayin'? - This is, this is New York.

Yes, I know the rent is gonna go up,

but the gluten-free pasta is kind of worth it.

Yeah, but I wanna see a cat.

Planning a wedding is so stressful!

Come on, man, I don't know why you're so stressed about this.

You're getting married to the love of your life.

Didn't you get like a wedding planner or something like that?

No, do you know how much they cost?

I watch a lot of wedding videos on YouTube,

I could do it for like 800. But I do like a minimal fare sort of thing.

- Yeah, thank you, thank you. - Small invite list.

An article Which is good, because I read We're doing it together!

That said that couples that plan together stay together.

- What was that, a late daily? - No, it was a meme on Instagram.

How do you know that she's the one? Jessie.

don't know.

I guess I don't think about it.

I guess we both just don't overthink it.

What if you're in a relationship

and you're both like prone to overthinking things, then?

If you need to get over this girl, you need to delete all the apps, okay?

No Venmo, no Instagram. No Twitter, none of it.

Because if you don't, you'll be getting into this space,

which is like this weird spiral depression.

Where you become very annoying and a hypochondriac.

- Did I tell you that I found a lump? - Where'd you find a lump?

- Right there. - That's your Adam's apple.

That's not what the internet said.

- So you're gonna reach out? - No.

That would just make her mad, so I'm not gonna do it.

I'm just gonna fall back, give her her space.

- That's it. - Really? No grand romantic gesture?

That stuff is the take-me-back-culture thing.

No, that's toxic, it's a disease, and I'm gonna be the cure,

even if that means I never get to tell her that I love her.

Right, you've told her that you love her.

Yeah, but I mean tell her I love her and mean it, you know?

Like, I love you. Like, like... what's that?

Incense, Jessie loves it.

She likes bodega incense?

Wendy cherished New York

for its endless encounters with the people you love

and the places you learn to love them.

Sir.

By now, you've probably figured out

that I am that soothing, old voice you've been hearing

holding your hand through this tale of commitment.

Did I mention that I also moonlight as a voice-over artist?

Hang on.

- Wendy! - Hey!

- Hi! - Cole, what are you doing here?

My job.

What's up?

- You okay? - Yeah, I'm great.

I'm great, I'm not here to see Milo. What?

- What? - Who said that?

No, no, I'm here to... To go to a meeting.

- I'm here to go to a meeting, a meeting. - Here?

No, no, no, no, no, just in the area.

It's this way.

- Okay. - So bye.

- Bye. - Bye.

I love a good New York love story.

The city it's one of the only places where you could...

- Hi. - Hi.

What's up?

Just a quick question. It's nice.

Is Milo upstairs?

Yeah, nope.

I don't think so.

Cool. Cool. Did he maybe say when he was gonna be back?

If he's maybe gonna be gone all night or just like five more minutes?

- Wendy. - Right.

- I hate to be the one to tell you this. - Okay.

I think he's seeing someone.

Okay.

Okay.

I'll see you.

I'll see you, Wendy.

Little did she know that Milo wasn't seeing anybody

and was, in fact, painfully single.

And where better to doubt your own singlehood

than under holy matrimony at the very bar in which they met,

where love filled the air...

The wedding of Hank and Jessie.

I'm not sweaty, it's just really hot.

- Okay, I'm nervous, I'm nervous. - You're gonna do great, man.

- How are you so calm? - Of course I'm calm.

I'm marrying the love of my life.

- I'm proud of you, man. - Thanks.

- I'm so proud of you. I really am. - So what are you gonna say to her?

- Who? - Don't "who" me.

I don't know who you're talking about. I love you.

- Bring it in. - Thanks.

And you are not an ugly Jon Hamm, I take it back. You are a hot Jon Hamm.

Everyone, please take your seats.

The bride and groom would like to share their vows

with us tonight and with each other.

- Jessie. - Yeah.

The first day that I saw you, I pointed at you

and said, "I am going to marry that girl."

I know.

- Jess, it's my vows. - Okay, sorry.

- Okay. - You go.

No, stop Not yet! Stop, don't do it yet.

Sorry.

- Start over. - Okay. First day that happened.

- Yes. - I was doing it as a joke.

But you have kept me laughing ever since.

I promise to be your best friend and to love you always. I love you.

I love you.

Hank, a lot of people say that cheesy thing

where they're like, "I don't always like you, but I love you,"

but I like you and I love you.

And I don't even care that you always fall asleep

the second we pick a movie,

and I don't care that sometimes

you only respond "ha-ha" to my texts and don't add additional info.

And I really love that we both like that meme

about birds that look like old ladies wearing hats.

And I just love you so much

and I'm the luckiest girl in the world that you love me, too.

Is that good? You like that shit?

Fashion moment.

- Same time. - At same time?

- Okay. - One, two, three.

You may now kiss the bride.

All right, let's get drunk.

Do you not want consistent sex without the emotional attachment?

I want that, but I also want the emotional attachment.

The words "I love you," in that order,

cannot be shared with one party to the other.

You just gotta pick a flavor and then just go with that flavor.

I care about you so much, Milo.

Will I see you again?

Yeah.

- Hello. Hey, hey, what's up? - Hi, hi.

How's it going?

I really miss you.

I really miss you.

And I would really like it if you were back in my life.

I'd like to be back in your life, too.

And I promise I'm done trying other flavors.

I just want one.

I love you so much.

I love you, too.

Once upon a time, in a magical kingdom known as New York City,

there lived a happily married couple.

Then there was Milo and Wendy or Wendy and Milo.

Maybe it was vows, the ubiquitous feeling of romance,

or the magic of Manhattan,

but they finally had true love's kiss,

and the heartbroken learned to love again.

Their thread began again and they finally dated happily ever after.

For a few more months.