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Hey, everybody.
It's Meredith.
So the other day, I was talking to our producer, Jasmine, about the first season of the podcast.
And I was telling her how one track mind we were, how every episode was about how to get over a breakup.
And she said, oh, that's interesting, because actually, I'm going through a breakup right now.
And it's a complicated one.
I don't want to get too into her personal life, but it's somebody she lives with.
And it's really hard.
And I was telling her about an episode I love called Don't Look at the Cupcakes.
It was really one of our first episodes.
And it was all about social media.
And what we're allowed to shut down, what we're allowed to block and how much of our ex we're supposed to see online after a breakup.
Jasmine really liked the idea of listening to this episode.
So for today, we're going to play this episode, which I still love, and it still surprises me.
I hadn't heard it in years, and I was laughing and relating to the people we interviewed.
We'll play it and then, after we play it, I had a conversation with Jasmine about what this made her think about, about rules for her own life and about how timeless some of these lessons are.
Because, even though this was our first season and social media platforms have changed so much over time, a lot of these lessons are absolutely true in 2026.
Also, Jasmine has a really interesting spin on social media and what it's doing for her right now.
So enjoy this special episode from The Vault.
Don't look at the cupcakes.
Stick around for a conversation with Jasmine and me about what this episode means, what we can learn from it and why it sort of still feels relevant.
I'll also say that we have new episodes coming very soon.
They are very funny.
Some are sad, but they always wind up funny.
And please, if you have new thoughts about Don't Look at the Cupcakes or have opinions about how it applies to now, let me know.
We can always be reached at lovelettersatboston.com.
From the Boston Globe, this is Love Letters.
I'm Meredith Goldstein.
I was dating this guy.
Let's just call him Keith.
This is Taylin.
She lives in New York and works in social media for Self magazine.
She's 23.
I knew her back when she used to live in Boston.
And I remember she fell hard for this one guy.
I kind of clung to him in a sense, because we were both you know two black people in a very like non-diverse environment.
So I just kind of felt like, oh, wow, I really need to get to know this person.
And when we dated, things seemed like it was a honeymoon phase.
So this honeymoon phase lasts for six months.
Talyn gets close with Keith's family.
And next thing you know, his mom became my hairstylist.
So I felt like our lives were kind of intertwining together in multiple ways.
And so begins the tangling.
You meet the family.
You connect to your new partner's friends on social media.
You even follow their mom on Instagram.
Things go well for Taylan and Keith until they don't.
The honeymoon phase ends.
He says he wants a more open relationship.
So she breaks up with him.
But there's just one thing.
I still had all of these connections to him via social media.
I unfollowed him, but I didn't unfollow or unfriend any of his friends, or even his mother or his sister, because I was like these people didn't do anything to me.
They just happened to become a part of my life because I was dating someone that was close to them.
Talyn blocks Keith, but she still has this window into his life through these other people.
From afar, it seems harmless.
Oh gosh.
So here's where things get really complicated and when I realized I probably should have cut things off a lot sooner.
So it had been about five months since we'd broken up and you know, I was still following his mom on Instagram and his mother posted pictures from a birthday party that she threw for him and she posted a picture of these cupcakes, and she had little photos of him printed on the cupcakes, and on one row of cupcakes was a picture of him and this girl.
And I recognized the girl in the photo and it was his ex-girlfriend.
When you first saw the cupcakes, like how long did it take you to process?
What was on there and what did you think?
Oh my gosh.
So I it was just kind of like a wave of anger and betrayal and something snapped in me and I felt like the crazy ex-girlfriend.
And I sent him a long, lengthy text message.
Hope you had a fantastic birthday.
Glad to know I wasted five months of my life with you as a total rebound.
It's always the girls they tell you not to worry about.
I hope you guys are happy.
I hope I never see you again as long as I live.
Waving emoji.
And, yes, so I truly felt like I was a crazy ex in that moment.
I just kind of wanted to hit him where it hurts.
And looking back on it, I was like, oh, my God, why did I do that?
I think that breaking up used to be easier.
Still hard, still awful, but easier.
Your relationship didn't hover over you like a ghost with every swipe of your phone.
Back before Facebook Snapchat, Instagram and all the rest.
There was no tagging, no notifications, no worry that a picture of your ex on a cupcake with an old girlfriend would show up in your feed while you waited for the subway.
It used to be that you just broke up and then tried to avoid each other at the mall.
So, as I said last episode on this season of Love Letters, I'm trying to figure out the best way to get over a breakup.
But how is it even possible to move on when our lives remain so entangled?
I put this to my sister Brett, who you heard from in the last episode.
Sometimes, when I read all the letters that come in to me, I feel lucky that we did not have to start our dating lives in the age of social media.
That when we were teenagers, when we were in our early 20s, up until my late 20s, If somebody broke up with me, I didn't have to look at them.
They were just gone.
I would be like full blown crazy, like way crazier than I am now.
Like I can't even imagine.
Especially because everyone's life on social media, like Instagram or whatever like, looks all shiny and gorge and like amazing and happy, happy right.
And it's never really like that.
And you know that when it comes to like friends and family, but when it comes to an ex, And then God forbid, that ex is dating somebody who's like ridiculously hot.
I don't know.
It's a nightmare and I am so glad I'm 44.
Dear God.
I've always struggled with this in the column I write for the Boston Globe.
I can't tell you how many letters I get from people who have trouble managing these connections when they're in a relationship.
Then the relationship ends and it only gets more complicated.
Take this letter I got recently.
Hi, Meredith.
My boyfriend's ex-girlfriend seems to be overly jealous.
They broke up years ago, but they're still friends on Facebook and she follows all of his friends and family's posts and likes everything his sister posts.
It makes me feel uncomfortable that someone wants to keep up with their ex's life so often and continuously.
We are very happy and committed to each other and have a growing future together.
Do I have to worry that this girl is constantly going to be in the background keeping up with our lives?
Signed, she likes it.
When I responded to her, I told her to give the ex-girlfriend the benefit of the doubt.
Like, lots of people think it's harmless to stay connected on social media.
But is it?
I asked Brett what she would advise.
No, no, cold turkey, cut it off.
Or I remind them over and over and over again, whatever you're seeing is 70 to 99% bullshit.
Like I try to basically say, you have to have perspective on this because remember, your social media feeds bullshit too.
I think mine is actually pretty accurate.
It's like a picture of my inhaler.
Yeah, well, it's you.
You're also old, dude.
I see Brett's point, but I know it's not easy to quit cold turkey.
When I saw one of my ex's wedding photos posted on Facebook, I knew I shouldn't have clicked.
But of course I clicked.
I clicked on every single photo.
This made me think back to Taylynn's story.
Here she is, a social media expert.
And yet, like the rest of us, she looked.
You never know what little piece of info is going to set you back.
Like cupcakes.
Or, in my friend Gina's case, a breakfast sandwich.
Hi, Gina.
How are you?
Hi, Meredith.
I'm doing great.
How are you?
Gina's a writer and editor living in Philadelphia.
She's 30 years old.
She told me recently about a breakup that she went through a few years ago.
For now, I'm going to call him Bob if I refer to him as a name.
His name is not Bob.
My ex and I met at the end of college in Philadelphia.
They were psyched to fall in love.
They were just starting their lives.
But they were different people.
And over time, those differences only became clearer.
It was us kind of trying to play house to solve something that we both knew was already broken, but we weren't really sure how to put an end to it.
The breakup is pretty standard.
Career stuff, space stuff, personal growth stuff.
Their goals just don't line up anymore.
We've been getting into a lot of fights about very inconsequential things like TV shows.
I think we were arguing about something on Game of Thrones.
And I just, you know, I said something and I realized he wasn't listening to me at all.
You know, it was just kind of like his eyes were like glazed over.
And I just I felt in that moment that he was not in love with me anymore at all.
I said, we can't keep doing this anymore.
And, you know, at the time he actually agreed.
The breakup is mutual, but it's still painful.
I was devastated when we broke up.
I cried for two months straight.
But life goes on.
She assumes there's closure, that there's no confusion.
Except there is.
He actually showed up at my house about a year later unannounced and just kept texting me and calling me and I wasn't answering because it was late on a Sunday and I was a little confused as to why he was texting and calling so many times.
And does he text first or does the doorbell ring?
He just kept calling and then he texted and said are you home or come outside or something, and I realized that he was there.
You open the door, you see him on your doorstep.
Does he look like what do you see in front of you?
So I opened the door and I was I was definitely shocked.
I don't know.
He said he wanted to talk to me about something.
So then I said he could come in.
Have you ever walked away from a social interaction and thought, wait, was that so awkward?
Should I have said something else?
Because I have all the time.
If you've also had this experience, check out the podcast Were You Raised by Wolves?
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So what did you, in your mind in those few moments, what do you think he's going to tell you?
I was trying to figure it out.
I mean, I thought something that very bad had happened.
But what does he tell you?
We sat down on the couch and I was like, okay, what's going on?
And he said, do you know that I can see your Venmo transactions?
And I was just.
It was so out of the realm of anything that I had been thinking that I had no idea what to say to that.
I shouldn't be laughing because this is like listen, I have been on the other side of this where I've concocted like completely strange and untrue narratives based on what I see on social media.
So I'm trying to have all of the empathy.
But what did he then, I mean, what did he then explain to you that he had seen on your Venmo?
He said it's making it really hard for him to move on to see that and he doesn't need to see who I'm getting brunch with.
And I was trying to think what he could possibly be talking about and I realized I had...
Venmoed my friend Joe for a breakfast sandwich with our running group because he had forgotten his credit card.
And he obviously thought that maybe I was dating Joe and, you know, from that transaction.
Before I get any further in this story, let me just pause here for a second and elaborate on what Venmo is, just in case you don't know.
It's an app that lets you pay people instantly, but the transactions are public, unless you make them private.
So your friends, or in this case, an ex, can see who you're buying a breakfast sandwich for.
The app is also sort of amusing because you can leave these little weird messages in the comments to tell people what you've paid for.
You can leave little notes or single emojis inside jokes.
So you can write whatever you want as the cause of transaction or what you're paying for, like you said you know, for sex, or like um for last night, even if it's just, like you know, some sort of household bill.
What are some of like the funny things that you might say in a venmo transaction with a friend?
Oh man, i mean, i could take a look at it right now.
Let's see, slip this money to the pizza guy when you go in for the left handshake.
Use this money to pay for your new peg leg.
A chicken emoji, a pumpkin?
Some people just have an eggplant emoji.
You can totally see where someone's mind could go with this.
Obviously they're saying something sexual, even though that bill is not for anything sexual.
But it's just a lot of eggplants.
But apparently, Bob does not understand this at all.
And who could blame him?
An ex is an ex, and his mind wandered.
The breakfast sandwich bothered him a lot.
Did it ever occur to you when you signed up to stay private, in terms of just keeping the profile private?
It did not occur to me to stay private.
I never even thought about it.
Everyone using Venmo knows it's a joke.
I think then the issue comes in when people who don't know it's a joke are using Venmo and get confused, or when people just try to interpret what it could mean.
So he's staring at you like you have well, I guess, like revealed this thing you didn't want to reveal, which you didn't care about revealing this breakfast sandwich that you purchased for Joe.
Controversial breakfast sandwich.
What do you say to him?
I was so just completely baffled by that accusation.
So even if it was a breakfast sandwich for Joe, that meant something more than a breakfast sandwich.
The accusation was ridiculous anyway.
You know, I think I just said... what's your point?
And then he got into the whole thing about not wanting to see what I was doing and that he tried to go on dates, but it was too hard and he could only think of me.
So it was almost like the Venmo was just an entry point for him to tell me how lonely he was.
But it seems like unfair because short, you were clearly having an easier time than he was with a new life, right?
But Sometimes things look easier than they are.
I'm sure you did not post pictures of the moments where you were like super lonely in your apartment or not having brunch with Joe.
Like that's not the part of people's lives we see.
I got very angry because I felt like I had done more work in dealing with the breakup than he had because, at least you know, for a month or two after that breakup I was a complete hermit, did not leave my house, did not want to see anyone, sobbed for days and days and put on you know the saddest playlist I could think of and, just you know, cried my heart out.
So I think that I felt angry at him because I had grieved and cried and then come out and been better and he had done nothing and was still coming back to me and telling me that I was too happy, and It was like he wanted me to take on the responsibility of his emotions as well as my own and feel guilty that he couldn't do what I had done.
And I didn't understand what he wanted from me.
I think that what people that are kind of struggling with that and struggling with stalking their exes is, first of all, you need to stop doing that.
And then, second of all, you need to instead kind of focus that energy on maybe joining something new or going and finding a new group and, you know, finding something where you can focus your energy in an outward way instead of in that interior way where you're just going to create a story that's false in your head.
Gina, thank you for sharing your story.
And I'll be following you on Venmo.
Excellent.
Or don't.
No, thank you so much for having me, Meredith.
It's been a pleasure talking with you about this.
Here's the thing.
Showing up at Gina's house to vent about her Venmo transactions?
Not a great look for Bob.
But I still have empathy for him.
Even the smallest bit of information can be too much.
Maybe a total social media blackout seems like overkill, but I really think that's just what's best.
At least until you've healed in some way on your own.
When I spoke with Taylin, the social media expert you heard from before, she said it best.
I just seriously should have just blocked everything, like ceased all communication, as I took the time to heal and understand and feel better about moving on from the relationship.
But If you know in your heart that you won't be able to move on seeing photos or seeing status updates or just any kind of small tip off relating to this person, it's best to just do the ban.
Save yourself in that sense.
You have to prioritize your own mental well-being.
There's a part of me that wants to think we're capable of staying connected, at least online, and that maybe we should see some of what our exes are up to, because otherwise it's like putting blinders on.
And that doesn't seem healthy either.
But after thinking about Gina Bob Venmo and talking to Taylin, I think we do have to censor ourselves.
When breakups are still raw, you start to invent totally weird narratives in your head.
Even when a breakfast sandwich is only a breakfast sandwich.
After a breakup, we have to protect our hearts as much as we can.
We're bound to see things that hurt us, but we should do everything we can to avoid them.
So, go forth and block.
And block liberally.
You're not deleting your history.
I promise that's still all yours.
You're just giving yourself the space and distance to heal.
And then hopefully, later, you can tangle up with someone new.
And now my conversation with Jasmine, our producer, who's going through a breakup with someone she still lives with.
Here's how she feels about social media as she changes what she wants to see online.
So yeah, I mean, okay, for context for me, up to Really recently, I did not have social media.
I took everything.
I didn't delete everything, but I took it off my phone.
I never looked at it.
So no Instagram, no TikTok, no Twitter, nothing, nothing, nothing.
And I did that to save my brain from the brain rot.
And I'm going through a breakup right now.
So I feel incredibly lonely.
We're sleeping in different rooms.
We live together so I can't really avoid her, and I'm home alone all the time because it's cold as hell.
Right now it's January, so for me, listening to this, I actually had the opposite reaction.
I re-downloaded everything because I'm so lonely and and it's somehow giving me the opposite.
Like I'm, I have comfort now because I'm seeing a world beyond me and I'm not seeing her.
I already see her every day.
I wonder how I would be if me and my ex didn't live in the same place.
And I see her looking at my stories still, but that's not weird from the next room yeah, from the next room.
You know it's not weird, I don't know.
You speak to a specific experience that I think a lot of people, especially in cities where everything is expensive, go through, which is like if you are still in that person's physical space, you don't need to create narratives about what they're doing.
I mean, I do wonder if it would be very different if she were elsewhere.
Yeah.
If you're at a point where you are not interested.
You are excited to explore new narratives and not stuck on the thing.
I can see how it wouldn't even be that hurtful to see somebody having a good time.
I think it's interesting, listening to this episode again, that I am reminded that Gina allowed herself to grieve and needed to grieve.
I knew Gina at the time of that breakup.
It was pretty epic.
It was like we could either spend the rest of our lives together and get married or probably not.
I think for Bob, this idea that he probably pushed it into a box.
By the time Bob showed up at her door, Gina was was probably okay with seeing pictures of Bob because she had really let herself let go.
But you're in this weird state where right, you have to remember that when this looks different, there's an outside world.
Also, Venmo stalking is a whole nother level.
So I mean, this episode is hilarious to me because Venmo was so brand new that I felt like I needed to explain it.
But I will say even this many years later, I am still a little surprised by people's publicness, And it's funny.
When I started with Venmo it was like things like an eggplant.
And now I see my friends absolutely paying babysitters.
Like you see the narrative gets a lot less interesting and less spicy.
And I have voyeurism for couples that pay each other publicly, who live together, married people for like, a cleaning person where like, you're telling me how you're doing your home finances and I don't need to know that.
It's just really weird.
The concept of Venmo- As a social platform.
Is odd to me.
And I do think also when we've had a social platform for a while-
The novelty has worn off about let's leave a funny message.
I think a lot less people are public now because again, with Love Letters the advice column piece of Love Letters the first few years a lot of the letters were about snooping, breaking into people's accounts.
I've broken into my boyfriend's whatever account and see that they've emailed somebody, whatever.
And I thought at some point, oh, people are snooping less.
But it's not true.
It's just that, first of all, we know more because of social media.
So everybody, who needs to snoop when you see where your person is all day?
But the other thing is, we have two-factor authentication accounts now.
You can't snoop in the way that you could.
It's not that people are less likely to do anything.
It's just that we've locked it down.
There's identity theft we know of.
Like, I don't think people are as cavalier about what they say or what they post.
Well, the other thing that struck me about this episode too, is as a newly reconverted Instagram user.
I'm going through and seeing the changes that have happened since I've been off.
And one of the things I'm seeing a lot is this specific ad that says are you checking who's looking at your stories?
For that one person.
Yeah.
I want to see if I can find this ad.
I'm very interested in algorithms.
It feels like it's speaking to me.
Instagram knows I'm going through a breakup.
Well, Instagram.
So the other day I was talking to two friends who are a bit younger and they were telling me what they get in their feed all day.
You know, when there's like a repeated sort of offering that it gives you.
And I said something like, well, all of Instagram is Kate Winslet talking about women aging.
And they were like, we've never seen that.
Oh, my God.
But it's for me.
They're giving me Kate Winslet.
And they're giving you, we know you are going through a breakup.
How do they know?
I don't know.
How do they know?
Sometimes I love targeted things because I'm like, yes, I do want that baggy sweater.
Oh, here it is.
PSA to my girls checking to see if he saw your stories.
Waiting for their texts, delaying your response, overanalyzing a non-existent future.
This is called preoccupied attachment.
OK, you know, I get some of these two, but that's also because I love letters like I get a lot of.
But also, don't you think that it's age and gender and they're just guessing?
I think they know I'm a millennial woman.
Yeah.
So you're probably stressed about somebody.
And I wonder, I wonder if they have some kind of thing that's like if you check your story's view count, you get fed this specific ad.
And I do check my story's view count because there are specific like, because I'm back on to Instagram.
I'm checking it to be like, who are the people that like care about me, who are interested in me.
And I'm like kind of shocked that like a bunch of, I mean, that sounds like a humble brag.
It really isn't.
It's I'm shocked at the people that I barely talk to are consistently looking at my things.
Yeah.
It's weird.
I I'm so bad at social media.
And for those who follow the love letters Instagram account, I'm sure you can guess that when it's very good, it's because I haven't done it.
Somebody else has decided to take over, but like, I also feel like it's like your habit.
If you're somebody who is a TikTok person, you are.
If you're like watching Instagram stories, you're watching all that are offered to you.
And it never really occurs to me to even do stories.
And then the other day, somebody said to me, oh, and they put it on the grid.
And I was like, well, I put everything on the grid.
Like there are these changes, right?
Of like, oh, the grid is like, you might as well tattoo it, right?
The grid is sacred.
And I really not so much age, because I do feel like I'm actually at an age where a lot of my exact peers live on social media.
It's more that I am a real candidate for brain rot with that.
So let's forget it's there.
But I just also was thinking about, it's funny hearing Brett on that episode.
I forgot she was in this episode, but she has since been married for years more and then been divorced.
And when they were close to deciding to get a divorce and to break up, Their social media habits changed a lot.
And there's now something I see where I'm like.
This is a couple that is now posting a lot, potentially in an effort to remind themselves how much they love each other.
And also the what we would now call like a soft launch of almost singledom.
We're like you know.
You see a high school friend and suddenly they're like posting to Facebook, of all places, a picture of them wearing a jean jacket, and you don't know why.
And I'm like, oh, wait, are they getting a divorce?
We're like, what's happening?
Right.
Even in 2018, we didn't have names for these things at that point.
But you now hear a different story, see a different story in that.
Maybe Meta and these social platforms know that if you don't use social media often and you come back on, you're probably going through some kind of life event, and vice versa.
Yeah.
Yeah.
And for me, like often it's I feel like the world is moving on without me and I feel lazy and I feel like I should be promoting this podcast.
I feel all these things where I'll be like wait, I got to do that, or I want to promote a friend's book.
Right.
But like.
But I also know that if I, if I let it sit on anything again, it's why I get Kate Winslet content.
I'm not shocked, but I think it is easier now to curate and manage expectations and manage accounts and ban yourself from certain things, because I think we're just savvier about it than we were when I made this episode.
I don't think as many people would punish themselves for needing to block because there have been so many studies and so much literature out there about how all of these platforms can mess with you and how they're not even good at it.
Back on.
Twitter went from being a highlight of my day to the worst part of my day, to something I'm not even really on.
So that isn't even called that anymore.
So I think as a culture, we're better about self-protection.
I do fear and I wonder if you can speak to this that what I now get which it sounds like you get too is a lot of information about relationships where it'll be like are you anxious now attaching?
Are you real friends?
Don't do this.
And real love, and it's like a lot of it is like men are bad but they can be good, but don't accept this, but do accept this and they are.
It's content that can really mess with you.
That is presented as self-help Yeah.
Well, that's a whole that's a whole thing.
The self-help explosion, the like weaponized therapy speak.
I mentioned that because this is the social media problem is like you're going through a breakup.
You go for me.
I'm going on TikTok.
I'm scrolling and I'm like. does this feel like you?
Do you feel like, and I'm like, that does feel like me.
And I watch it to the end.
I'm like, okay, I got something out of it.
But now the, now the algorithm's like, oh, you watch that to the end.
Here's some more crap about like abusive dynamics or not.
I did not have an abusive dynamic.
Yeah.
Amicable breakup.
But you know it's it's, it's almost like it wants you to think, like suddenly everybody's got a narcissistic ex.
How did that happen?
We can't all be narcissists.
No.
And also like, someone who prioritizing themselves doesn't make them a narcissist.
So if they don't love you because they just want to do their own thing, that just sucks.
That's like a whole other thing.
But I think it's hard.
It's just hard.
And so now what I say is it's not even just about blocking an ex.
Sometimes it's about blocking the account that is telling you over and over that there's a problem to diagnose, and blocking the TikTok account that says you're dating wrong, or or blocking the account that gives you a thousand red flags to look for, because by the end of the day you're only seeing red flags the naming of problems.
And I know we've made fun of that on this podcast.
A lot of just like you know, they're pocketing you.
They're all these terms that are like, whatever.
And I'm like, also dating is awkward.
And sometimes people aren't doing any of those things.
They're just making missteps and it's trial and error.
And they're trying to do what they need.
And they're looking for what you might be doing to hurt them.
So That would be my 2026 add to this, which is that it's not just people we have to protect ourselves from before we're ready to see them.
It's also like if you're reading an Instagram account that is just like four Canva words on a page and you're like yeah like, just go like take a walk something.
I don't know.
It feels.
Yeah, no, that's very wise.
You don't protect yourself from the ex and their social media presence and the orbit around that.
Yeah, protect yourself from the algorithm, the breakup algorithm.
It will get you.
It'll get you and the dating, the dating fatigue algorithm, because it wants it wants you to feel bad and it wants you to feel like, if you just tweaked a few things you, you'd emerge like a phoenix, you'd outsmart the system of humanity, which no one can do so.
But did it make you feel better to be on no social platforms, to hear, to hear gina?
Yeah yeah no, i.
It makes me thankful that, even though i'm i'm going through this kind of rough patch in my life at the moment it could be worse i i, i.
One of my favorite seasons, not just because it was our first, but based on topic, is that we spent eight episodes that first season talking about breakups, because and i love that we talked to people like gina, who i don't want to say she was, had it better.
But you know, i'm sure if we had interviewed bob, it would have been an entirely different story.
So hearing during that season from people who were going through it, who were long out of going through it and had survived it, it's just um, it's formative to make changes that that like this.
So I'm reminded of the importance of these stories.
Love Letters is a production of the Boston Globe.
I'm Meredith Goldstein.
Thanks for listening.
