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The end of baseball season can be bittersweet.
If your team didn't win the series,
you're left second-guessing decisions made along the way
and hoping you get another season to get it right.
Steph, I know the flight leaves in 72 hours, okay?
And I am thinking about it. It's just...
P.J., it's on you. What are you gonna do?
All right, look, Steph, I gotta go, okay?
I gotta pay attention.
Steph. Steph.
Steph. Steph...
All right. Steph, I'm hanging up on you.
Who was that?
Dude, I love her to death,
but she is driving me crazy.
All she wants to know is who I'm bringing to Italy.
Really? Seriously? You guys are that bored?
Enquiring minds wanna know.
I thought you were taking that botanist guy, Ethan.
Evan.
Yeah, I thought so, too.
But then he ditched me with "I'm swamped." Remember?
Thanks for bringing that up, though.
So now I've got three days to find this perfect date to Italy,
and it's driving me crazy.
Well, if you're willing to let go of perfect
and will consider sad and pathetic,
I see four options here.
I'm an option. Pick me. Pick me.
I'd happily take one of you guys.
But, come on, what's in it for me?
Well, first of all, Kenny Moritorri.
Enough said. No, no. Say more.
Moritorri? Moritorri?
I got family there. Where?
Some in the heel. Some in the toe. Some in the calf.
What if I were to tell you that my family owns a villa in Florence?
And parlo italiano perfetto senza l'accento.
Really?
Who cares about that? Everybody over there speaks Italian.
Take me, and I'll be your personal valet.
I'll carry your luggage, I'll hail cabs, and I promise, I won't be creepy.
This time. Wow.
Well, I hate to burst your bubbles, fellas,
but history teaches us that P.J. and I are excellent traveling companions.
Costa Rica. Mmm-hmm!
Six days in a shack in Puerto Viejo.
Beer, surfing, beer, shrimp tacos, beer.
This is true. This is true.
You know, it's interesting. We travel all over the world
and go to museums and see sights,
and we don't see a lot of that same stuff in our own city.
Oh, come on, dude, Chicago's got nothing on Italy.
I mean, the food alone is worth traveling. Not true.
Visciglia's on Erie, hands-down the best Italian food on the planet.
Many Italians agree.
They got a great manicott.
And wannabe Italians.
Look, I love traveling.
I'm just saying, there's so much stuff to see right here.
These last few weeks, me and the family went to the zoo,
the aquarium, the planetarium. And it's been great.
That would be really fun to check out some Chicago sights.
I mean, there's some pretty great things I've never seen.
Let's each pick a place we've never been, and we'll all go,
like Ferris Bueller's Day Off.
Yeah, I'll do it. I think that sounds awesome.
It'll be one last hurrah before I start my new job.
See, I was in until he said "hurrah."
"Hurrah" means drunken adventure.
I'm back in.
What, you guys are serious about this? Yeah.
I don't know. I mean, playing tourist all day? It seems kind of...
Oh, what's the word? Uh, lame.
I used to sound like you,
when I lived in the 'burbs and my soul was dead.
But I can fix that.
I guarantee you'll see something you've never seen before.
Yeah, I don't... Ah, ah, ah!
No need to thank me. Your smile will be thank you enough. Huh?
Boop! Huh?
Wow, last night was amazing.
I canceled our trip to the Sistine Chapel.
Breakfast?
My auntie made me a bowl of Capitano di cruncho.
Capitano di cruncho?
That is impressive.
I assume. I said,
"Me and my man would like to have breakfast in bed, please."
Oh, my God, I had the weirdest dream.
Was there a boyfriend in it? 'Cause we're two days away from leaving.
Who are you bringing?
Do you remember our philosophy professor, Dr. Hevly?
You're bringing Hevly?
He's, like, 100 years old.
No.
He said something I always liked.
He said, "Before you make these big life decisions,
"consult your soul in a cool, quiet hour."
So who are you bringing?
No one. I am going alone.
Excuse me?
The pressure of finding this perfect date was tainting the whole trip.
I mean, when did I become this crazed girl
whose happiness is all tied up with finding the right guy?
Six months ago,
when we agreed to devote ourselves to finding the right guy.
Look, I know you're not psyched about this,
so I have a little present for you.
What?
I'm gonna let you pack for me.
Please. You think just because I have extraordinary packing skills
and a sixth sense for combining outfits,
that you can bribe me with it?
T-shirt, tennis shoes,
Cubs jersey.
I'm done.
And you can't find a date to go with you to Italy?
Shocking.
You love my family. I do love your family.
You cross out my idea?
No, I didn't cross out...
What's going on? Hey.
We are mapping out the day-off itinerary.
Yeah. We each picked a place we've never been.
I picked the Sears Tower.
Mike picked "in the company of a satisfied woman."
Hey! You got one! Did it feel good?
Hey, Bobby, how are we gonna do all that stuff?
We have the Cubs press conference tomorrow.
I know. They're just announcing some roster changes.
Get Pete to cover for you. That's what I'm doing.
I would, but I'm taking two weeks off to go to Italy,
so I feel like I should be there.
I'll go for you.
Please. I need an excuse to not go on this dumb-ass field trip.
You keep talking like that, and nobody's gonna wanna sit with you on the bus.
Hey, Andy, where'd you pick?
I'll give you a hint.
There's a desk, a phone, and it's my new office.
Oh, man! You're not going?
The new job called and they asked me to start early.
You're bailing on the day off?
Come on, man. This whole lame thing was your idea.
I am still committed to you having a great time, Brendan.
I'll be with you in spirit.
Hey, I thought I'd find you here.
Evan!
Oh, um, you remember the guys. Yeah.
What's up, man? I'm Andy, her brother.
What's going on? You got a second?
Yeah, sure. Yeah.
Um...
Hi. So how are you?
I'm good. How are you? I'm great. I'm great.
I just got back from Belize,
and I wanted to see you.
Wow, from Belize.
Yeah. We had an emergency situation down there.
One of my advisors discovered a new species of plant.
So I flew down there to assist him,
only to learn that what he really discovered
was amanita muscaria.
Oh...
Yeah. He was shrooming his ass off.
Oh!
But he's fine.
Mostly. Yeah.
Thinks he's Batman.
Keaton? Kilmer.
So, listen, I just wanted to say that I was
really enjoying your company,
and I'm sorry I disappeared like that.
Oh.
So you really were swamped.
Totally. But I have some time off now, and...
You know, this might sound crazy,
but I was wondering if you wanted to come
to my parents' lake house in Michigan.
You know, we could play some Risk, go canoeing,
I don't know, roast marshmallows.
Do your parents live in a summer camp?
Kind of. Except with better liquor, and there's no talent show.
God, I would love to.
But I'm actually going to Italy in, like, two days.
No. You do not wanna go there.
This time of year, it's mosquitoes and fat people
and that annoying accent.
No, wait. That's Michigan.
Well, I don't even know if it's possible, but, uh,
try and have a good time.
I'll try. Um...
I'll call you when I get back.
I would love that.
Okay. Great. Thanks.
Bye.
You guys really that bored?
Yeah. Yeah.
Michigan? Ugh!
Hello.
There's a problem.
I can't find any clothes in your closet I like enough to pack for you.
Guess who I ran into? Evan.
Evan? Cute Evan? Evan the botanist?
And get this. He really was swamped.
He even invited me to his place in Michigan.
That's perfect.
Did you invite him to Italy instead?
No. What?
Why not?
I am going alone, okay?
I consulted my soul in a cool, quiet hour, remember?
Well, consult it again. Okay?
Keep consulting it until it tells you that Evan is the one...
Hey, Stephanie,
I think it'd be really fun to wear makeup in Italy.
Oh, you think I don't know what you're doing,
but I do.
You're going to need eyeliner, mascara,
blush, tinted moisturizer...
Thirty-two years old, you've never been to the Art Institute?
What, did you skip elementary school?
On the giant list of things I'm not interested in,
museums fall somewhere between ballet and arena football.
Hot chicks hang out in museums.
Museums are creeping up the list.
So what do you think?
I mean, it's big, and that's cool.
You know, years ago, I was...
I was fighting with my family
'cause they wanted me to take over the Newman Trust,
and I wasn't sure about it.
So I came here, and I ended up staring at this painting.
You see, on one side, you have this opulent building
and a lot of faceless people, right?
And on the other side is a couple,
simply walking together in the rain.
And it kind of made me realize that I had a choice
to make my life about simple pleasures and people,
not money and status.
Wow,
I just thought it was big.
Seems like this place holds a lot of memories for you.
Yeah. I guess you could say that.
Mmm-hmm.
Hello. Hey, buddy. You see anything good today?
Hey, buddy. Yeah. Bet you're glad you're not here.
Are you kidding? Do you know how bad I wanna be with you right now?
I was this close to calling in sick
just so I could expose you to new things.
Uh...
That probably sounded creepy out of context.
You know it was just a bored phone call. I know.
He's calling me from work just to torment me, I know it.
Pretty great, huh?
I used to come here with my dad all the time.
I thought we were supposed to pick a spot we'd never been before.
Well, that's the thing. I've been here dozens of times.
I've never been there.
Are you afraid of heights? Yeah.
Well, when I was a kid,
you know, my dad would try and get me to the top,
but I didn't have the guts.
I'm a grown-up now, so I'm sure it won't be a problem.
Made it, Dad.
Hey, man, you should really try to make it these last 20 feet.
The view is incredible.
Dude, there's a full half inch of glass
between you and splat on the pavement.
That wasn't very supportive, was it?
I think I'll just hang back here.
It's okay, Kenny. We're proud of you.
Hey. Hey. What's up, buddy?
I can only stay for a second. I'm on my lunch break.
Oh, check this out. You can see my new office from here.
It's right there.
There. Under the helicopter.
So, Brendan? See anything good today?
Well, you know, if I squint really hard,
I think I can see Wisconsin, so that's just, um,
magical.
Not to worry.
Still have a trick up my sleeve.
Yeah? All right.
Uh...
I gotta go. See you losers later.
See you.
Oh, shoot, me, too. I gotta go to that press conference.
We're actually going now, if you wanna...
Oh.
Thank you. You did good, buddy. I'm proud of you.
I feel like I can do anything.
So, traded to the Brewers, huh?
Yeah. Um... Yeah.
You know, at first, I was bummed.
But then I spent the night thinking about it,
and I realize it's a good thing.
A really good thing.
Well, yeah, a change of scenery is always great.
I have a huge crush on you. Well...
What?
Sorry. I'm done trying to be cool.
Since I'm no longer a Cub,
there's no ethical roadblocks keeping us from having dinner.
That's one of the good things.
So let's have dinner. Or breakfast, or both.
Okay, wow!
Um,
I would love to, but I am leaving for Italy tomorrow, so...
Really? With your boyfriend or...
No, with my friend.
And her boyfriend.
No, that doesn't sound awkward at all.
Okay, it's a little awkward.
Well, okay. Um, I have some free time,
but traveling around Italy with a gorgeous woman,
eating great food, drinking wine...
Well, I'd hate to be the fourth wheel.
I will call you when I get back.
You better.
Don't look back. Fight it.
Fight it.
Hey! Hey!
How's it going? So? What do you guys think?
It's the beach, man.
Sand and water. Not much to think about.
I don't understand. You've never been here before?
Nope. Grew up in that building right there.
This is the first time I've ever stepped foot on this beach.
That's crazy.
Why wouldn't you come over here?
I wanted to, but my parents wouldn't let me. They said it was public,
which in rich speak means "dangerous and dirty."
Yeah, dude, you better be careful.
That golden retriever will lick you to death.
Anyway, this is the whole reason I wanted to come down here.
Get a view of Chicago I'd never seen before.
Well, actually, Bobby, I wouldn't...
Let him go.
You guys, the view from out here is awesome!
Great. Why aren't there more people in the water?
Didn't I read something about an algae bloom?
I love you, Chicago!
Yeah, we'll stop at the drugstore later.
Yeah.
Big wave! Big wave!
Yeah, so now he's been traded to Milwaukee,
so there's nothing standing in our way.
Well, does the cute former Cub have a passport?
Steph. The universe sent you two perfect men
who both said, "Take me with you."
If I were you, I would just...
Oh, my God. I have to call you back.
Thorn? Hmm.
Hi.
Uh, hi. Oh, my God. This is so weird.
What are you doing here? I thought you moved to Seattle.
Uh...
Sorry, no. I Just... I flew in just now to interview Barack Obama.
Fancy. Yeah.
Wow! How are you?
How, um...
How's married life?
I'm good. I'm not married.
Yeah, that never happened.
We got along great when we were hunkered down in Kabul,
but, apparently, put us in a house in suburban Seattle
and epic fights.
Oh, God. I'm sorry.
Yeah. It's...
Well, you'll always have Kabul.
I can't tell you how good it is to see you.
I was gonna call you after the interview.
Have dinner with me tomorrow night.
Oh, my God. I would love to. I am, um,
going to Italy tomorrow.
Oh, wow. Yeah.
Well, um, have dinner with me there.
What, in Italy?
I have an open schedule.
Is there a better place to have dinner?
Um...
Wow, you really like dinner, don't you?
Among other things.
Um...
Guys, the good news is I think my feet and ankles are finally thawing out.
Oh, yeah. There's no way to get in that lake
without your balls jumping into your throat.
Please. Oh, sorry, poopy.
Hey, did I show you my art?
Take a look at this.
Oh, yeah.
Nice, huh? No way.
I'm gonna have it framed.
You're gonna hang this on your wall? Yeah.
Mike, that's a big step. You don't have anything on your walls.
I never had art before.
Now I have art.
Hey, what's up, smiley?
I saw you chatting up that cute hostess over there.
Yeah.
I got digits.
Look at you.
Wow, first the Sears Tower, then talking to a really hot girl.
I am enjoying The Kenny Show today.
Well, you know, it's been an extraordinary day for all of us.
P.J. had two different men resurface
and offer to come to Italy.
What? Are you serious? Who's Number 2?
I thought it was just Evan. It's actually three.
What? Who's Number 2?
The cute Cub. Who's Number 3?
Thorn. I just ran into him.
Thorn!
Stop.
I thought he was getting married.
He broke off his engagement.
Oh, my God!
Can we please appreciate how weird this day is?
I know. Believe me, I don't even know what to think.
Stop thinking and pick one.
Steph, I am going alone, okay?
I will call them all when I get back.
Boo.
Oh, come on!
What is wrong with you? Embrace life.
What are you talking about?
I just spent all day sightseeing instead of packing and working.
I'm not saying you're not adventurous and deceitful.
I'm saying when it comes to matters of the heart,
you protect yourself, you hold back.
Please.
Look at the facts.
You have three fantastic men available to you.
Six! Pick one!
I'm no longer available. I wasn't including you.
No. There are too many ways for this trip to go wrong.
It's just not worth the risk.
What risk?
Having too much fun?
Falling hopelessly in love?
Nothing good ever happens when you play it safe.
This is true.
Can't let fear rule you.
Although there is an argument for looking before you leap.
'Cause seriously, guys, my ankles itch a lot.
All I'm saying is, you and your brother are great
at motivating people to do great things,
but when it comes to your own life, you pull back.
That, of course, up there is the Sears Tower.
Oh, my God!
Ladies and gentlemen, you are a wonderful crowd,
and I would like to play one of my favorite tunes,
and dedicate it to a man who thinks he didn't see anything good today.
Brendan Dorff, this one's for you.
No, no, no. Wait, okay? Look, I did see something good.
Uh, Mike got turned on to art, Kenny busted out of his shell, Bobby got a rash.
Too bad. I'm gonna sing anyway. Hit it.
♪ Danke schoen
♪ Darling, danke schoen
♪ Thank you for all the joy and pain
♪ Picture shows, second balcony
We love you, Andy Franklin!
♪ Was the place we'd meet, second seat Whoo.
♪ Go Dutch treat, you were sweet ♪
Wanna go halfsies on a coin sorter?
Oh, I'd love to. Yeah.
God, where is P.J.?
Hi. Thank you.
Oh! Thank God. There you are.
Sorry I am late. Hi, Lance.
I can't believe you showed up alone.
Do you know, actually, Stephanie, I took your advice,
and I consulted my soul again,
and it turns out there was somebody
that I wanted to bring to Italy.
Oh?
So I called him, and I invited him, and he said yes.
Really?
Excuse me. Thanks.
And he's not here.
I waited for him outside and he didn't show up.
Oh, my God.
Oh, Peej.
Wait. Wait, wait, wait. Who? Who did you invite?
Flight attendants, crosscheck for departure.
Oh, wait! Oh, no!
Shoot!
You know what? I was fine.
I was fine, and then I listened to your advice,
and now look what I am.
Can't even get my damn bag in the damn overhead.
Penelope Franklin?
I'm sorry.
The gentleman has upgraded your ticket to first class.
We have a glass of champagne waiting for you behind those curtains.
What?
Allow me to stow your luggage.
Thank you.
You made it.
Who is it?
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