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To take a moment and think about who your perfect wing person would be.
Who knows you best?
Who knows what you're into and what you're not?
Who do you want riding shotgun?
Maybe it's a friend or a sibling.
Or maybe it's that person who knows that even though you work from home in pajamas, you can clean up nice when you actually try.
But let me throw out another idea.
What if the Okay, hear me out.
Who has a better read on you than a former partner?
They know your charms, your quirks, your weird obsessions.
They know what turns you on and what turns you off.
Now, I'm not talking about somebody you had a terrible breakup with.
If there were lots of tears involved or hard feelings.
If there's still seething resentment, then no, this is not your wing person.
I'm talking about the ex-
It just didn't work out with.
Maybe the spark wasn't quite there.
You were two different people.
Your relationship was never going to go anywhere anyway.
So you're still friendly.
You're still in each other's lives.
You still care about one another.
When you think about it, who better to vouch for you?
To give you that little blue verified checkmark that signals to the next partner yeah, this person is a catch.
You should totally go out with them.
Across a couple of continents, over 100, many Twitter exchanges and with a lot of jokes along the way.
This is precisely the role that Alessandra played in setting up her ex-boyfriend Michael with his new love, Zoe.
Here's Alessandra.
All of like the reasons why Michael and I weren't a good match and we were great.
Platonically, she had
And that therefore makes their connection even stronger.
Do you feel that your experience with him and your then friendship and then interest in this setup like that?
It counted for more with Zoe?
I agree with you 100 percent.
The endorsement of it, you know, he was vetted, essentially.
From the Boston Globe and PRX, this is Love Letters.
I'm Meredith Goldstein.
When it comes to some of my own exes, I like to think that I would have been a pretty good wing person as they looked for their next partner.
Not that they ever asked for my help.
Take Kyle, my high school boyfriend, who was on the first season of the show.
He is so smart.
Literally, he could probably do research that could cure a disease.
And once he made me a mixtape that I still cherish.
If Kyle hadn't met his wonderful wife on his own, I would have happily found him one.
For today's story.
I'm going to start with Michael Serio, a 27-year-old comedian who lives and performs in Chicago.
By way of backstory Michael was born in Chicago, grew up in Denver, went to college in Ohio and then returned to Chicago after he graduated.
Michael says his friends used to make fun of him for being a serial monogamist.
Had a couple girlfriends in high school got to college.
Really just had one girlfriend from college for three to four years.
We broke up. right after college.
Michael is single when COVID shuts everything down in the spring of 2020.
And this is when he meets Alessandra.
Michael and Alessandra had both gone to Miami University in southwest Ohio.
When they were students.
Alessandra had seen Michael perform with his comedy group, but they'd never actually met.
What first brings them together is Twitter, specifically Joke Twitter, a corner of the social media platform where comedians and comedy fans trade jokes and witty banter.
She found me on Twitter and just kind of followed me, thought my tweets were funny, this and that.
I did the classic slide into her DMs because I was like, oh, we have a lot of mutuals.
My best friend was actually in her sorority when she was in college.
The reason why we started talking was because one day, I believe it was May 1st, 2020, I
My best friend, my roommate.
She got into medical school and we had drinks and we were kind of drinking all day.
And I had tweeted something about how I was still, you know, drinking.
And so he DM'd me and said, are you good?
And I said, no, I'm fine.
We're just celebrating.
It's during this flirty back and forth over Twitter that Michael and Alessandra discover that they actually live super close to each other in Chicago.
At this point, it's mid-2020, only a few months into the pandemic.
Everything is closed.
It's hard to get around the city or really do anything at all.
Meeting someone new or dating, it all feels pretty impossible.
Alessandra and Michael are both single, bored and lonely, which is why, when they finally meet in person, they decide what the hell?
Maybe we should just get together.
Right off the bat, once we figured out that we were a block away from each other, we got tested.
We went into each other's places and really it was a lot of watching movies, a lot of taking walks, a lot of cooking together.
We cooked a ton together.
With no comedy shows going on or clubs open.
Michael and Alessandra also spend time workshopping Michael's live routines in her apartment.
He would do bits for me and he would work on his comedy in front of me and I helped flesh out certain characters with him.
We would troubleshoot.
We'd brainstorm ideas.
And a couple of the characters that are really, really popular right now when he does shows are actually characters that I helped develop with him.
But over time, Michael and Alessandra realize that the physical intimacy, it's just not there.
This seems to be a sign that maybe they are not destined to be romantic partners.
She goes.
We're really like an old celibate couple who are sitting on our couch watching the Muppet movie, watching the entire thing, muppets like we watched a ton of the muppets.
That was the.
That was the kind of thing, but it was like.
It was like yeah, we'd go out, we'd make a ton of food and then we'd fall asleep.
It sounds amazing.
It was, it was comfy, it was so comfortable.
But also we're like we are 24.
Maybe this isn't how we should be spending our life at 24.
By the fall of 2021.
Roughly a year into their relationship, Alessandra has already been talking to her therapist about how this thing she has with Michael doesn't feel like it.
Michael is feeling the same, especially as the world starts to open back up again.
One night, they finally acknowledge this to each other.
He had a show and after the show we went to a bar and we sat there and I looked at him and I said you know, we're not going to get married, right?
And he said, oh yeah, I know.
And we were like, yeah, okay, cool.
It was really a relationship of comfort at a time where everyone was looking for companionship because so many people were trapped inside their COVID pods.
The breakup was really hard because It felt like I lost my best friend.
We did not talk for probably about a month because we needed space.
But I was worried.
He's a great friend to me, and I didn't want that chapter to end.
I texted her about a month later and was like, hey, I have your Tupperware.
Can I return it?
And she went, yeah.
So that's when we started hanging out as friends.
I have this theory that some of the breakups that I was most upset about and relationships that I clung to later I would realize I was just so worried about missing the friendship.
Like, it's not like I wanted to keep dating them.
I just wanted to not lose the friendship.
And sometimes I didn't.
So when you guys started hanging out as friends, was it like, Oh, okay.
Like it felt better to both of you.
Completely.
It was like, we kind of knew it.
We were just hanging out the way we were before.
Cause once again, we weren't really physically intimate towards the end of the relationship.
So it was nothing new.
We would just sit on opposite ends of the couch and watch a movie and just like talk and chat.
We realized we're like, oh, we are truly much better friends.
After the breakup, Michael resolves to stay single for a year.
He's been in a series of relationships by this point and he starts to wonder who even am I as a person when I'm not coupled up?
Meanwhile, in the spring of 2022, Alessandra decides to spend a month in Madrid.
She's been working remotely, so she can pretty much go anywhere.
One weekend she takes a trip to Barcelona to see a different friend she'd met on Twitter, a woman named Zoe.
Alessandra and Zoe had gotten close over the past couple of years.
Zoe had been there for Alessandra when a different relationship, before Michael, had fizzled out.
The guy I had been kind of seeing at the time was broke up with me when I was alone in Portugal.
So I had got on the phone with Zoe and she comforted me.
And that was what kind of solidified her as someone who I trusted and someone who I could tell really cared for me and I cared for her.
So back to 2022.
Alessandra, Zoe, and a couple of other friends spend a few days together in Barcelona.
This is Zoe.
She came over and it was just like a really fun like girl time.
We went out to bars.
We visited a bunch of museums.
Mainly, I think it was me playing like the tour guide and, you know, showing the girls around.
One night, they're all out together.
Here's Alessandra again.
We were in the smoking section of this club.
These guys come over and try to chat them up.
And Zoe, she's not having it.
She, you know, go away.
She is so mean to these guys.
She is so much more assertive and meaner than I could ever be.
And it was so cool because you know when someone's and I don't mean that in a very negative context
It was just like if someone is bothering you or if someone is really aggressive towards you.
She knew how to handle that very efficiently.
Later that night, they're back at Zoe's place in Barcelona.
There was two people on a fold-out couch and then two people on an air mattress.
And I was sitting on.
I was laying in the air mattress at four in the morning, or like 430, five o'clock in the morning, after we'd come back.
And I was texting Michael saying, you won't believe what happened today.
Zoe was just so, you know, she knows how to tell a guy off.
He was very like, okay, I really want to hear more about this girl.
That was the light bulb.
I was like, oh, okay.
I need to tell him more.
Alessandra doesn't yet have a clear picture of where all of this will lead.
All she knows is this.
She's got two friends, one of whom happens to be her ex, who seem kind of well matched.
The story continues after this short break.
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We're all out of the ordinary.
There's a battle playing out right now over who should control American universities.
We're going to bankrupt these universities.
In season one, we were guessing what was to come.
Now we know.
We want nothing less than $500 million from Harvard.
From the Boston Globe and on the media, it's season two of The Harvard Plan.
This time, it really is personal.
Listen wherever you get your podcasts.
Okay, we're back.
So it's super late on a spring night in Barcelona in 2022.
Alessandra is lying on an air mattress, and she has this epiphany.
She starts to see all the ways in which her friend Zoe would be a much better fit for her ex-boyfriend Michael.
Alessandra, who's then 25, works as a tech consultant for higher ed institutions.
She's from Milwaukee.
She is a huge Bucks fan.
In style and sensibility, she says, she leans more corporate.
Zoe, on the other hand, who is 24 at the time, is an aspiring filmmaker who works as a social media content moderator in Barcelona.
She was born in Mexico and grew up in Ireland, the Czech Republic and France.
Zoe is an incredibly intelligent, creative, spunky, beautiful girl.
She takes no shit, but she is someone who will go to the ends of the earth for you.
Michael, for example, He's a performer.
He's more artistic.
He loves movies, and I honestly don't really watch movies.
Zoe loves film.
She loves talking about French film.
Her style like literal physical, like clothes and stuff like that aligns more with, I think, what Michael was looking for.
The more Alessandra thinks about Michael and Zoe, the more she plots to hook them up.
I really wanted them to get together, because I...
I knew Zoe separately.
I knew Michael separately.
And I thought, oh, these two would, this would be good.
So Alessandra starts to hatch her plan a little more openly.
Here's Zoe.
I think it was the last night the girls were there.
I showed them what we do in the Shadows movie because I told them like I love the show and like this is like Such a great movie.
It's so funny.
I love it.
We should watch it.
And so we watched it.
And then she was like, that's one of Michael's favorite shows and movies.
Like, you would get along with him so well.
Was there any part of you that was like, wait, she's dated him?
Initially, yeah, definitely.
I think that's why I was very hesitant about making a first step and everything.
Because to me, I was like, oh, maybe it's awkward.
Not just for me, maybe for her as well.
So I was just like, I don't really know about this.
After Alessandra returns to Chicago, she, Michael, and another friend go out to a bar one night.
She starts slipping in little things about Zoe to me.
She goes, oh, you know, Zoe's really funny.
She's really cute.
She has a big personality, which I know you like.
Like, here's a picture of her.
Take a look at her.
And Alessandra the entire time is like rubbing her hands together.
Like she's Gargamel from the Smurfs.
And she's like an evil matchmaker.
Cassandra's romantic scheming works.
Michael decides to message Zoe directly.
Zoe tweeted something about tartar sauce.
And she was thinking about sauce you use with steak tartare.
Because I'm guessing in Europe they have a completely different type of tartar sauce.
And I said, God, I hope you're not putting tartar sauce on steak tartare.
Real romantic stuff, right?
Oh, yeah.
This is like the language of...
Sexuality, yeah.
Real hot-blooded romance, pulp novel stuff.
And she responds to me, feed me steak tartare.
Okay.
And I was like, well, I guess I'm in.
There are other exchanges too, including one about Neil Young and music and a jokey back and forth about red flags and green flags.
Michael and Zoe soon move from Twitter to text messages.
30-minute voice memos traded back and forth continent to continent.
I guess it just happened so naturally.
You know, it started with very getting-to-know-people topics and then it just started getting a bit more personal.
And I felt like he was someone that I could really trust.
Before Michael, dating was always kind of like a performance thing.
And I think what was different through exchanging these voice memos is that I slowly realized like wow, this is someone I can actually be myself with, even though he isn't here.
Like, I feel like I'm being myself.
I'm not being whoever I think that he wants.
We have a lot of good banter back and forth.
And I was like, hey, why don't we have a date?
And she goes, yeah.
And I'm like, why don't we cook the same recipe?
And she goes, yeah, yeah.
So we cook a recipe together.
It was a rigatoni vodka sauce pasta that my family makes.
After a few months like this, Michael decides it's time for him to meet Zoe in person.
He loves talking to her every day and the connection he feels is strong.
But how can either of them be sure what this is until they're actually with each other?
They make a plan for Michael to come visit her in Barcelona for two weeks in October of 2022.
Zoe agrees to pay for half his ticket.
We liked each other so much that it was a week before we left and we were talking about like this and that.
I said just offhand, not even thinking about it.
Oh, I love you.
And I texted her and I went, well, maybe not.
Maybe let's do it.
And she literally respond.
She goes, I almost said it back just casually, too, because it was just so it just felt so natural.
I'm like, let's meet each other first.
Both of them recognize that there has to be a traction for this to work.
So they make a pact before Michael visits that if there's no spark, they'll be open about it with each other.
Zoe even has a futon for Michael to sleep on if that's how it all goes down.
It was very much like, let's go into it without big expectations.
If we see each other and the physical thing isn't there, we'll just have a great two weeks as friends.
If it is, all the power to us.
As you prepared for this, how much talking with Alessandra did you do about a state of things?
I think because I was so nervous about what it was and like we hadn't really discussed making things official until he came over, I think I kind of wanted to keep it to myself because I didn't really want to jinx it.
If you met somebody online, right without a mutual connection, who you'd met in person, there is this added layer of like a stranger who could disappear or whatever.
Like Did having her as this real-life connection make all of this feel a little bit more secure before he arrived?
Yeah, for sure.
If I didn't know Alessandra, I don't think I would have pursued it the way that I did.
I think definitely, like, I mean, it's Michael and I love him for him.
But I think I would have been way more wary and cautious about letting a man that I've never met coming over to stay at my house.
On the plane ride to Europe, Michael is a hot mess.
He's trying desperately to sleep, but he can't.
He pops a handful of Benadryl, which only makes him more delirious.
He can't stop his mind from racing.
I'm like gripping my seat, trying to fall asleep, but I'm so like antsy.
And this is I'm like, oh, like, OK, let's not make it a big thing.
Let's not make it a big deal.
Just if it doesn't work, it doesn't work.
It's fine.
It's fine.
It's fine.
When he was on his way and he was soon to arrive, what was going through your head?
I was nervous because I really, really liked him and I knew that he really, really liked me.
But I guess I was kind of second guessing, like maybe I'm delusional.
Maybe I read things wrong and maybe like maybe he just wants to be like good friends.
And like I just read too much into it.
I didn't know if the spark that we'd had over the phone was really going to translate once we met.
I land in Barcelona, I walk out of the pass security and she's standing there and she gives me a big smile and I go.
Oh my God, she's gorgeous.
This is the woman who I fell in love with over the phone in real life.
And I walk out and she, she comes up and she gives me a hug and we just kiss each other immediately.
And it was like the connection was immediate.
He came out and he just looked so out of it.
It was really funny.
His eyes were red and kind of like teary, and he was just barely responding to what I was saying to him.
And I was just there like, oh my God, I'm so happy you're here.
Like, it's so nice to finally see you.
She gets a cab back to her place and the entire time she's just holding my face because she's like I can touch you now.
This is so weird.
It turns out that Alessandra's instincts They are spot on.
Michael and Zoe's first time being together is everything they hoped it'd be.
In the days that follow, Michael and Zoe see the sights in Barcelona.
They have lunch with Zoe's sister.
Michael meets Zoe's friends.
Her father takes them out to dinner and starts referring to Michael as Miguelito, which Michael takes as a good sign.
And then one night they're out at Zoe's favorite dive bar in Barcelona.
And she is like, before we go out and have a good time getting drunk tonight at this bar...
I want to make sure when you said you love me over the FaceTime, did you mean it?
I'm like, yeah, I meant it.
But, you know, we should have met each other first.
Like, I wanted to make sure that she goes, oh, totally.
I want to know.
I just want to make sure.
And I'm like, I'm like, yeah, yeah.
I'm like, I do love you.
She goes, oh, good.
I love you, too.
And she's like, I guess we're dating now.
I'm like, yeah, we're dating now.
This trip to Barcelona is the first of several they take back and forth to be with each other.
Zoe flies to Chicago just a few weeks after Michael's visit.
On her first trip to his turf, she gets to see him perform.
She meets some of his friends.
And, of course, they meet up with their fairy godmother Alessandra who, by this point, is getting regular updates from both Michael and Zoe about their developing relationship.
Here's Alessandra again.
This was one of the first times that I'd seen them together.
And we went to a bar and we were sitting there and all they did was talk about French film.
And I was sitting there like, I have nothing to contribute to this conversation.
They locked in.
They were absolutely locked in.
And I was like dang, like obviously the relationship didn't.
You know, our relationship didn't work out because our interests and what we wanted were so different.
However close Michael and Zoe's connection, it is hard for them to date long distance like this, especially being in different countries.
Flights are expensive, for one thing.
They're now trying to figure out what a future would look like and where that future might be.
But because of the remote communication skills they learned during COVID and because their partnership began as this slow burn thing, they're actually pretty good at long distance.
Talking every day on FaceTime, talking every day on this.
That's the normal for us.
And that's how we've developed our relationship.
And because of that, a lot of our relationship really is based off of conversation talking, loving each other's personalities.
Plus, the time difference, it works for them.
Especially when you're dating as an artist, as a comedian.
It is hard to date people who have nine to five jobs, because the time I'm available, which is during the day, is different than a lot of the times other people are available, which is at night.
Because she lives overseas.
It has made it so much easier because I can talk to her during the day, which is her night.
This past November, Zoe flew to Chicago to visit Michael.
They spent Thanksgiving in Denver, where Zoe met Michael's family for the first time.
What do you enjoy most about actually getting to be in the same place?
It's just different being able to go to a physical location, look into his eyes and talk together and like just bond, I guess, over new and different things.
The date potential is way more.
Like, we can go to the zoo now.
It's not just like, oh, what movie do we want to watch today?
What video game do we want to play together today?
What recipe do we want to cook today?
We still can do all that, but we can do more now.
And we can kiss each other while doing it.
Yeah.
Fair, fair.
As for Alessandra, well, she's got her own serious boyfriend now.
Where did she meet him?
Where else?
On Twitter.
Not on joke Twitter this time, but on Bucks Twitter, as in the Milwaukee Bucks.
She says they are very much planning a future together.
I ask Alessandra if there are other people she's set up besides Michael and Zoe.
She says she's made recommendations before, but nothing quite like this.
How proud are you of yourself?
Do you get smug?
Of course I get smug.
Of course I do.
Do you feel like you're owed a bunch of dinners?
How do they repay this gigantic favor?
Oh, we've already talked about it I am their kid's godmother.
Wow okay, yeah.
Oh, they've already said yeah yeah, you're gonna be the godmother.
That just seems like a situation where you then have to buy somebody else more gifts.
I don't know, I don't know how that.
I feel like you need more than that.
Fair enough um no I, I do get a little smug I, but I'm mostly, I'm just so happy that for them, because they're great and I love them both and they're great for each other and I
Yeah.
So, of course, I'm just like, I did it, you know.
Love Letters is a production of the Boston Globe and PRX.
Today's episode was produced by Jesse Remedios and Scott Hellman.
Ned Porter does our audio mixing, sound design, and mastering.
Today's interviews were recorded by Andrew Merriweather and Emily Files.
Maddie Martell does our audience engagement, Love Letters Illustrations by Ali Riza.
Special thanks to Linda Henry.
Our music is from APM.
We're online at loveletters.show.
And remember, we are an advice column, so send your questions to lovelettersatboston.com.
I set up a couple that's still together 20 years later and there's nothing like I'm never more smug and like self-important and proud.
What I'm like, I, I did that.
I'm Meredith Goldstein.
Thanks for listening.
