Welcome to Love Letters.
I hope you don't mind, but I have been desperate to play a specific episode from The Vault and give some extra thoughts about it.
Basically, in our recent episode with Olivia Wilde, she and I kept talking about psychotherapist Esther Perel, famous for the podcast, Where Should We Begin?,
Esther Perel served as an advisor on Olivia's new movie, The Invite, which is getting fantastic reviews, by the way.
If you missed the Olivia Wilde episode, here's what I mean.
We said a lot about Esther.
Actually, something Esther pointed out when I said, Esther, the kids love the movie.
Like, young people love it.
Whoa, what do you think?
I was so shocked.
She wasn't shocked.
And she said, young people today experience their social worlds.
And I'm paraphrasing it.
Obviously, she said this with a much cooler accent and in way more eloquent terms, but in a curated fashion, heavily curated.
So they know where they're going, what will happen, who will be there, what their opinions are.
It's all kind of.
Curated ahead of time so that they know what the result will be because it better be worth it to leave the house and it better be worth it to interact and
I was telling Olivia Wilde that Esther had been a friend to Love Letters, that she's been on the podcast, but I couldn't remember which episode she joined us in first.
Then separately, in our last episode, with recent high school graduate Lila, I started thinking so much about my own high school boyfriend.
In case you missed that episode, here's where I mention him.
I knew a lot about myself that I had intended to be single as an adult, but I love Kyle.
And I was like, we all love Kyle.
And so I was like, we're staying together.
And I was incredibly romantic about Kyle.
I remember sending him all these notes from college and...
And then it became very painful because I was building this new life and it wasn't very present and he was in a world I knew that I missed.
Mm-hmm.
So, I re-listened to the Love Letters episode that my high school boyfriend was on, and randomly, going back to the beginning, it was the same episode that first featured Esther Perel.
So I wanted us to revisit it.
Truly, Lila's story had me so nostalgic for Kyle and our story.
And I remember feeling such appreciation that my own high school boyfriend joined us during our first season.
I wanted Lila to listen to the episode to see how hurt feelings can turn into something else.
So first we'll play the vault episode.
Then at the end, I'll give you some updates on what I think about the lessons from that episode and on Kyle.
Enjoy Kyle.
Enjoy Esther Perel.
Two people I'm so grateful have come on this podcast.
You'll also hear a bit at the top of the episode about our entire first season, which was all about how to get over a breakup.
Every episode explored one way to try to get through it.
Honestly, if you're going through a breakup right now, listen for the first time or all over again.
I'll see you at the end with some thoughts.
From the Boston Globe, this is Love Letters.
I'm Meredith Goldstein.
When I was little, my dad would say, you really want your cake and eat it too?
And I would say, why can't I have my cake and eat it?
Like, this is a ridiculous statement.
Patricia, as I'll call her, is a writer I know through work.
She went through a terrible breakup with a woman who was basically like her wife.
They weren't technically married, but they lived together.
They moved across the country together.
They even shared a cat.
Once it was over, they tried to repurpose their relationship into a friendship.
But it was way too painful.
Patricia learned that she couldn't have both freedom and the luxury of this person still in her life in a meaningful way.
She had to choose, have her cake or eat it.
Like, I agreed to breaking up with you, which means I do not get to have the sweet moments we had that a couple does, nor am I promised the sweet moments that friends have later.
I don't have a right to anything of you anymore.
Like, that's just truth.
And those people who think that they might still, because at some point you guys were together, are a little deluded, I think.
I don't know.
I mean, I feel like maybe I still have some of that churchiness in me.
But if a relationship is sacred, if sex is sacred, if sharing our bodies is sacred, then one would say like the aftermath of that is like dust, you know, like nothing.
You get nothing.
For Patricia, it was the length of time they'd been together that made it so impossible to be friends with her ex.
After so many years, they were in too deep.
If it's short and sweet and it doesn't happen, but we had a good time, I'm okay with the idea of being friends.
But years make it different for me.
Because I give myself a lot more.
I think we both do.
And then you start making plans and traveling, and that makes it different.
The weight of it is different at that point.
In the more than nine years I've been doing the Love Letters advice column, so many letter writers have asked me, should I stay friends with my ex?
But in the past year or two, it seems like there's a new thing going on.
People believe that the only way to really show that they're over someone is to be friends with an ex.
They feel like it's an obligation, something that says they're really over it.
But is a friendship with an ex the thing that helps you get over a breakup?
I wanted to get some expert advice on this question of post-breakup friendship.
Is it possible for everyone?
Should you even try?
I checked in with Esther Perel.
If you don't know about her, she's a famous psychotherapist who works with couples having relationship problems.
Before we get to Esther, though, I want to take a few minutes to share some of your stories.
All throughout this first season of the podcast, as we've explored these different ways of getting over a breakup, you've sent me your comments, your questions and your own breakup stories.
It's been such an honor and so great to read and receive them.
My favorite part of Love Letters has always been you, this growing community of letter writers and commenters who are telling me what to do.
Here's one of our listeners, Lauren, who sent in a story about trying to hook up with this guy she met on Bumble after a devastating breakup.
Let's just say it didn't work out.
Hi, my name is Lauren.
I had gone through a pretty serious breakup.
We'd been together for a total of about five years.
So needless to say, I was just definitely feeling pretty down.
So a couple of girlfriends suggested that I give Bumble a shot.
You do see people giving you a little bit of attention and that's kind of fun, but ultimately it just really kind of bummed me out.
I went on a few dates.
The first of which kind of escalated to us making out and was the first person I'd kissed since my ex and I started crying right there.
Ultimately, I just, it just made me feel, it all just made me feel worse than I had before.
But sex with someone new did serve a purpose for another listener who shared this story.
Hi, this is Laura.
I was married for almost 20 years, realized he just wasn't the one, so we split up and about six months later I found myself on my own in my new apartment and I was dating on Match
And I found a guy I kind of liked.
I was attracted to him.
We were dating for about a week and my friend said, go for it.
You should have sex with him.
It was a little uncomfortable because it was such a short amount of time, but I went for it.
It was sort of symbolic.
It was like
Just entering in a new phase of my life and I was curious about what it would be like to be with somebody else.
Now that I look back on it, I feel a little icky, but it was a good process to go through and now I have met the love of my life and I couldn't be happier.
Back in episode five, we talked about breakup accomplishments, those big things people do after a breakup to reclaim their lives.
One listener had an experience of his own to share.
Hi, my name is Harsh.
When a girl dumped me in January of last year, it was basically the biggest heartbreak of my life.
Lack of sleep, reduced appetite, lower focus, and just generally feeling super depressed about the whole situation.
But I decided to take on a lot of different activities to help me recover.
I started volunteering again.
I started going to the gym again.
I traveled a lot.
I took on a new job.
I moved to a new apartment.
Basically changed my entire situation so that I can refresh myself as a person.
At this point, I'm ready to jump back into the dating game and see what happens.
I was especially grateful to hear this next comment from Malcolm Astley.
Malcolm has been an activist on dating violence prevention since his 18-year-old daughter Lauren was killed by a former boyfriend in 2011.
Malcolm started the Lauren Dunn Astley Memorial Fund in her memory as a way to promote healthy relationships.
We need to be much more active, I think, in recognizing and attending to the needs of those involved in breakups, including providing peer breakup support groups, sound resources on grieving, which are needed with the end of an important relationship,
And instruction in knowing about and coping with the tough at-risk feelings like shame, depression, loneliness, rage, and contempt, and helping others cope with those tough feelings and dangerous ones in safe ways.
Thanks for helping us think about this fundamental human challenge and preventing harm.
Thank you so much, Malcolm, for your grace and for reminding us of the real stakes involved in breakups.
Look, there isn't one single formula for how to break up or for getting over a breakup.
I think we've learned that together.
But the more we talk about it, the closer I think we can get to figuring it out.
Okay, so back to whether or not you should be friends with an ex after a breakup.
I called up Esther Perel herself to see if she had any answers.
I get so many letters from people who say, you know, my ex-boyfriend wants to be friends, but I find it painful.
Why can't I do this?
So, you know, when two people break up, should there be an expectation of friendship?
I think that your question has to be put in context in terms of life stage, in terms of age, in terms of the nature of the breakup, in terms of the context in which this breakup takes place, if there are other people that replace one another.
Or sometimes they are, I care deeply about you.
I really love you, but I'm 27.
And I don't really want to settle down.
And you are in a different stage.
I would love for us to stay friends.
That's very different from I have been with you for 10 years.
I just have broken up with you because I just met another person.
Esther says that people sometimes want to have it both ways.
But you can't.
I'm not ready to really be with you.
But I also don't really want to lose you.
So I want to be in what I have often called a state of stable ambiguity.
You know, not too much with you so that I don't lose my freedom, but not too far from you so that I don't have to deal with my loneliness.
I think sometimes it's a way not to say goodbye.
It's an avoidance of the inevitable.
When you leave somebody, you have to be able to accept, no, you probably won't see them anymore or not soon or not immediately.
And you have to deal with the consequence of your choice.
It seems to me that the person who should be able to dictate these terms is the person who's getting broken up with.
That it's unfair as someone ending a relationship to say, I'm ending this and now you have to...
Have the following role in my life.
I tend to shy away from the demands and the should and the fairness.
There is no fairness in relationships much of the time.
You can ask what you want.
That doesn't mean you're going to get it.
What you see isn't necessarily what it is.
And so if you are not ready to be friends with the person who's breaking up, you just say, at this point, I need to lick my wounds.
At this point, I need to find comfort with the people who want to be with me and not the ones who give me crumbs.
After time passes, under the right circumstances, you can find friendship with an ex.
But that new relationship must develop under entirely new terms.
There's a time for it, and that's not necessarily when people are in the midst of the breakup.
But later, if the ending was in a context in which it wasn't one person deeply hurt the other, betrayed the other,
Breach their trust and so forth but just for circumstances of life the relationship finished
It is often a beautiful you know person who was important in my life and he continues or she continues to be important in my life but the terms are so very different it's
It's a beautiful transition.
It's a translation.
Certain things, their meaning changes, their existence continues.
That's wonderful.
Thank you so much.
My pleasure.
Thank you so much.
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Boston, New England.
Maybe you're from here.
Maybe you went to college here.
Maybe you live here now.
It's a place rife with smart people and big ideas.
Every week at the Boston Globe, Say More brings you the best thinkers and storytellers from around the region, like Dennis Lehane, author of Gone Baby Gone.
I loved growing up in a working class town.
I loved the loyalty.
I loved the jokes, the sense of family bonds.
I don't find that in a lot of the rest of the world.
Expertise with heart from all around New England.
From the Boston Globe, listen to Say More.
After thinking about what Esther Perel said, I wanted to check in with my sister, Brett.
By now you know that Brett's the person I go to about all things.
I'd been thinking about a former romantic relationship in my life that led to one of my best friendships.
Brett saw me through this breakup and then watched the friendship grow.
I was curious why Brett thought it worked.
I want your opinion.
Do you think the real badge of being over someone is the ability to be friends with them?
No, not necessarily.
I think it's great.
It's awesome if that part of your history sticks around in the form of a friend.
You know, I'm not so good at it because my boundaries can get a little sloppy at times.
I might end up like sleeping with them.
Like you are great with boundaries.
This is true.
I like have none.
There are so many people nowadays who feel like.
It speaks poorly of their relationship in general and their ability to be like good humans to each other if they can't pull off a friendship.
Oh, that's bullshit.
And you know what?
I do think that you can have a relationship with very thick boundaries.
But ultimately, if you're really looking for like, I mean, we have so little time in our lives, right?
If you're looking for a true friend, you have to be ready to hear about each other's dating lives.
And if you're not ready for that, then I'm not sure how hard you should push a friendship.
That's just my opinion.
The ex that felt most like a friend, the one I knew I would always know, is the first breakup I ever had, my high school boyfriend.
But I think that one of the reasons I broke up with him when I did was because I thought...
If we keep dating, we're going to keep hurting each other.
We're going to keep failing each other and I'm going to blow what is going to be one of the best friendships and longest friendships of my life.
I knew it then.
We started dating when we were 16 and 17 and now we are 39 and 40.
To this day, I can't quite figure out how we did it right.
Like, I'd love to instruct people on how to do it.
Because even though we broke up so young, for some reason, it was that much more hurtful then.
So how have we kept this so great for so many years?
You should ask him.
Do you really think I should ask him?
Absolutely.
Hell yeah.
What do you got to lose?
Good point.
What did I have to lose?
So I traveled back to Maryland, where I grew up.
And I asked him.
Hi Kyle.
Hi Meredith.
So I wanted to talk to you as an expert, as an expert witness, because, you know, I've been writing this advice column for like nine years.
Do you read it?
You don't have to lie.
I do not read it.
Okay.
I will not be offended by your lack of reading it.
You'd be very offended if you knew how often I read it.
Kyle and I dated in high school.
He was my prom date.
Our romance started when he came to my house and ate pizza.
And I remember we watched the Michael Douglas movie, Falling Down.
Halfway through the movie, Kyle turns to me and says, hey, Meredith, no one's fallen down yet.
And in that moment, I was like, oh, my God, this person is going to be my boyfriend.
And then he was.
But then I went to college, and he was a year younger.
We lasted for a bit, but we were so young.
I just didn't see how it was going to work.
Eventually it ended, mostly my doing.
There were some hard feelings.
But here's the thing.
We're still friends.
Like, real friends.
Like, if I had to call someone and really talk, it might be Kyle.
Now, I get it.
Kyle and I dated back in high school.
So, yes, friendship might be easier for us than for a lot of exes.
That said, I know many people who would never be able to be friends with an ex, even if the relationship happened like 20 years ago.
I was curious, though, what about our relationship allowed us to build this genuine friendship afterward?
And did he manage to pull this off with everyone he dated?
Well, I'm not friends with all my exes.
What percentage do you think you're friends with?
Well, social media-wise?
Okay, yeah.
Superficial social media-wise, tell me, and then for real, for instance.
I'd say maybe 50%.
Social media.
Social media.
And then I'm sure if I ran into...
90% of my exes we'd be cordial, but not like, you know, it would never be like an F you.
Okay.
Uh, I don't know.
Are there any ones besides me that are like an actual friend?
No, there's no one except for you that is still in my life that I used to date.
One thing that clearly helped us was the distance.
We dated, we broke up, and then I was already at college, so he didn't have to see me anywhere.
We didn't run in the same circles any longer.
I didn't have to hear about you.
Yeah.
And then through that, because if you remember, I think after we broke up, the next time I saw you was probably like a year later.
No, that's true, I guess.
And you came to Pittsburgh with your sports writing friends.
Oh, yeah, right.
And I think that was like the first time we had seen slash spoken to each other in, I mean, a year.
Oh, we went to the Andy Warhol Museum.
That's right.
That is the key to getting over.
Yes, the Andy Warhol Museum in Pittsburgh.
There were floating pillows.
There were balloons, yeah, a whole room of balloons.
I always forget about that trip.
And one of the things that that trip did for me was that like, I was able to be like, Oh, I love hanging out with this person.
Like it was not about, this is my prom date.
It was about like, I want to know this person as an adult.
And like, or I don't know if I was as conscious of it, but I say that's pretty okay.
Maybe I wasn't, maybe I wasn't that conscious of it, but I also knew that it felt natural to me.
Yeah, it did.
I remember because when you came down, I was actually at a party.
Okay.
18 year old, 19 year old guys.
And I was, I just, I left to come visit you.
Like it was, it was something I was excited to do.
Yeah.
So there was that feeling that I'm able to identify now.
There was a comfort with Kyle, a certain trust.
He was someone I knew I didn't want to lose forever.
After our romance faded, that foundation remained.
And it felt really important to me.
Not in a, I hope we fall back in love kind of way, but in a, I still need this person in my life kind of way.
There are some exes where, like, I can be happy that they're happy, but there's still 2% of me that is, like, rolling my eyes.
Yeah.
And with you, I can watch you be happy and I'm like psyched.
Like there's like 100% of psyched.
So I feel like that's when I'm thinking about telling people like when it's worth it to be friends.
That's I think a necessary part of it where like, I can feel a part of your happiness because I'm psyched.
You're happy.
Yeah.
Where I'm like, I just hope I get invited to the party.
Right.
Which is different than I'm happy.
They're happy.
And I'm like, whatever my jaw is tense.
Um, I, I,
Yeah, I don't know how to, I have that with no one but you.
Maybe the common denominator is that I'm amazing.
That must be what it is.
I didn't want to say it.
That my advice to everyone should just be like, it's just, you have to, I need to be your ex.
I think my job is just to lead you down that path till you come to that realization.
Okay play advice columnist for a second do you think my letter writers should feel a pressure to be friends with their exes
Now, why at that moment would you decide that you want to be friends with somebody?
That's the wrong time to decide, make that decision.
If you really want to be friends with your ex for whatever reason that is, you need to give it time.
It needs to be, you need to separate yourself from that person, maybe even that group of friends, and then come back together, reconvene at the Andy Warhol Museum in Pittsburgh and go from there.
My relationship with Kyle now is more like family.
Our birthdays are a day apart so we call each other at midnight every year between the two days.
On those calls I tell him that I love him because I do but it's fine because we both know it's a different kind of love.
I think there are certain people that you can be friends with that you have broken up with or ended a romantic relationship with, but that is not the rule, nor should it be.
This success story, you know, again, it's the only one I have.
So it's not like I have the formula for it.
It's just the formulas that we...
You know, together somehow, you know, it just happened.
It was the circumstances of our relationship.
The only constant is time.
And I would recommend time away from that relationship and the things that remind you of that relationship.
And I think if you have that, then there's a chance that you could become friends.
Thank you, Kyle.
You're welcome Meredith.
I can't wait for our next birthday.
Me neither.
So here we are.
I guess I figured out on the season of the podcast that there's not one universal way to get over a breakup.
And maybe that's not a surprise.
But by asking the questions, I've learned so much about how to get over something.
And I hope you have, too.
I've learned that time and distance are very necessary ingredients for moving on.
I've also learned that losing yourself in music can be cleansing and cathartic and perfect like George Michael.
I've learned that raising your value through some kind of post-breakup accomplishment can be great for your heart and for your soul.
I learned an unexpected lesson, which is that blocking your ex on social media isn't petty.
It's just a key thing to do to help you get over it.
I learned from my sister that rebound sex can feel very invigorating and fun, but also very awful.
Only do it if you're sure that's what you want.
I've learned that both parties in a breakup have big responsibilities, and that getting back together isn't something you can ever count on or wish for.
From Kyle, I've learned that friendship is possible, but only under entirely new terms, and probably a long way down the road.
I guess my big takeaway is this.
Take the time and space after a breakup to mourn the loss, because it is a loss.
But as soon as you start feeling ready, go and reclaim your sense of self, your agency, because you deserve it.
You've lost something, but you haven't lost yourself.
Not at all.
In fact, you may have even learned more about who you are.
Most importantly, I've learned that after a breakup, every day can feel different.
And when you least expect it, maybe after looking at a handwritten note from a former lover, maybe written in Sharpie on a crumpled Euro, you can find hope in what's next for you.
I hope you enjoyed that first season story from The Vault.
It's funny, when I listened again in 2026, I thought, maybe this episode makes friendship with exes seem too easy.
Kyle and I did have some really rough moments where I'm sure both of us thought, is this worth the work?
But he's right.
What we did allow each other to do was to take space when necessary.
And after a number of years, the space didn't seem necessary at all.
Last month, Kyle turned 48 and I turned 49.
We do not call each other at midnight on our birthdays anymore because we are older and I'm useless at midnight.
I think I called him at 9 a.m. on his birthday.
Listening to the episode again, I was thinking about how I said I could be happy for Kyle, and that if he was happy, I just wanted to be invited to the party.
Upon re-listen, that actually made me cry.
Because this is where I'll say that when he got married, early in 2020, I did get to be at the party.
We danced.
He had the Orioles mascot at his wedding reception.
And I wasn't there just as a friend.
I mean, that is what I am.
But I'm also a piece of his history.
I do hope I'm family, just like he's family to me.
His grandma was still alive at the wedding, and she saw me for the first time since I was 18.
And she was like, oh, hey, Mare.
And it was such a special moment to know somebody that long.
Also, Kyle is a scientist who's done some work with virus control and public health.
So a few months after his wedding, when the world shut down, I called him and asked, how long will this be?
I specifically asked, when will I be able to sit inside in a cheesecake factory again?
And he said, at least another year.
He put me at ease as much as he could.
He taught me all about the science of vaccines, and he was such good support from many states away.
And I kept thinking, I am so proud of him.
I will also say that quite randomly, on the day this episode is released to you, I have tickets to Weird Al Yankovic, a man I wouldn't think to see in concert if not for the mixtape Kyle made me when I was 18 years old.
Everyone should know that our Love Letters Friends with Benefits Club is growing.
Subscribers get ad-free episodes, bonus episodes, and extended cuts of episodes.
There's already a bonus sitting there waiting for you, and it's all about happiness, whether you're single or coupled.
Details are at the link in our show notes.
And if you want a little taste of our next regular episode, here's a teaser.
When I turned 70, I started saying, look, I don't have much time left.
There are things I still want to do.
And he never paid any attention to that.
And then when I turned 75, even more loudly, I started talking about
I'm 75.
I'm either gonna do it with you or I'm gonna do it without you, but I'm gonna do it.
You'll hear more from that guest in our next episode.
This Vault episode was produced by Jasmine Aguilera.
Remember, we're also an advice column.
Send your questions about relationships to lovelettersatboston.com.
When you tell us stuff and ask questions, others feel secondhand comfort.
I'm Meredith Goldstein.
Thanks for listening.
Your gay elders are calling, pick up.
Silver Linings with the Old Gays is a podcast hosted by four larger-than-life personalities sharing wisdom, laughs, and a little lovingly earned side-eye after decades of life experience.
They talk about everything from health and aging to relationships, queer culture, and the moments that shape who we become.
It's honest, hilarious, and surprisingly heartfelt.
So if you want stories that are as entertaining as they are meaningful, check out Silver Linings with The Old Gaze, wherever you get your podcasts.
