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Khalilah Holt
Pushkin.
Jonathan Goldstein
Hello.
Khalilah Holt
Hello. It seems like the spider has become the thing that catches the fly. You're welcoming me into the studio?
Jonathan Goldstein
Am I the fly? No, I guess you're the fly. I'm the spider. Feels pretty good.
Khalilah Holt
So. What?
Jonathan Goldstein
Yeah. As hopefully our listeners know by now if they're paying attention.
Khalilah Holt
Whoa, whoa, whoa. I was sensing a little attitude to.
Jonathan Goldstein
The don't antagonize the listeners.
Khalilah Holt
And that's rule number one in broadcasting.
Jonathan Goldstein
As our dear audience should know, we have been encoreing some episodes this summer, and usually at the end, we'll have a little update with the guests about what's happened since. Yes, this is gonna be a little bit different. I got to interview someone I was really, really excited to talk to. She makes one of my favorite shows. It's called Pen15.
Khalilah Holt
Yeah, we talk about it.
Jonathan Goldstein
We talk about it, like. Yeah, frequently. We do.
Khalilah Holt
Yeah. When it was running, we really. We talked about it a lot. I have to say, it's probably one of my favorite shows, too.
Jonathan Goldstein
For those who don't know the show, it is made by Anna Konkle and Maya Erskine, who are two real life best friends, and they play versions of themselves at 13. So it's about their middle school experience. They are playing themselves as adults, and then they are surrounded by literal children, people who are actually 13 playing their classmates.
Khalilah Holt
For the first episode, that concept felt like a big hurdle, maybe to kind of like get into the story, but I was like, over it and into it. Like five minutes in, you stop thinking about the fact they're adults. It's like a magic trick that they pull and it's beautiful and so funny.
Jonathan Goldstein
It's really great. I really think anyone who hasn't watched it, I would highly, highly recommend it. And I was very excited to talk to Anna. And yeah, we thought it could be a cool conversation to put with this episode because both of us are revisiting that same age. In her case, very literally recreating scenes from her childhood.
Khalilah Holt
Yeah. So you guys end up talking about the episode and her show and about.
Jonathan Goldstein
Just our respective middle school experiences.
Khalilah Holt
So let's get to listening, shall we?
Jonathan Goldstein
Let's get to listening. I'm Khalilah Holt, and this is Heavyweight. Today's episode Lathe, right after the break.
Anna Konkle
This is an I Heart podcast.
Jonathan Goldstein
I'm walking to work one morning when I spot Leif heading towards me. From the ages of 12 to 14, Leif was my crush, the object of my junior high obsession. I still Google him occasionally, but he's completely absent from the Internet. I have no idea what became of him. It's like he just disappeared. So when I see him on the street, I feel my heart speed up. I wonder if I should say hi. I wonder if I say hi in what tone I should go. Leif. Leif. Oh, Leif. But then, as I draw closer, I realize that the man I thought was Leif is not Leif at all. And in fact, is not even a man. He's a teenager. This makes sense, given that I've not seen Leif since I was 14 years old. Still, having your heart speed up at the sight of a teenager is a sure way to feel like a creepy. And just like that, to quote Carrie Bradshaw, Leif is back on my mind. All these years later, and I remember the exact type of pen Leif wrote with. I remember his birthday. I remember how he kept his wallet on a long chain, the first time I'd ever seen such a thing done. And wore a quicksilver sweatshirt with holes worn through the sleeves that he'd stick his thumbs through. He was pale with blue eyes, short and slight.
Lucia
I remember him being kind of like waifish, almost like. Kind of almost like ethereal.
Jonathan Goldstein
Crushes do not exist in a vacuum. They require gleeful gossip with your friends. And so I call Lychee, who's been my best friend since elementary school, to talk about our old classmate Leif.
Lucia
He had this, like, light blonde hair that he dyed and was not like a long, like, down to your butt hair, long, like, like a bob length.
Jonathan Goldstein
But like shaggy for men. Shaggy. There we go. A men's bob. Once, while away on a school sponsored trip, we phoned Leif from our hotel room, me, Lucia, and our other friend Emily. The three of us huddled together on the scratchy Marriott comforter, stifling our giddiness as we dialed.
Lucia
Oh my gosh.
Jonathan Goldstein
I don't remember if we actually talked. The thing I remember is that we called.
Lucia
Did we talk to his parents?
Jonathan Goldstein
We talked to his mom. Our friend Emily asked if she could speak with Leif. It's Emily, she said. Emily said, leif's mom, go upstairs and talk to him. Then she hung up on us. Turned out he had a sister named Emily. So weird. Lucia's stepmom was a photographer, and she once mentioned that if Leif and I ever started dating, she wanted to take our portrait. I don't think she knew I had a crush on him. Leif was just so short and I was so tall that I think she found the idea of us as a couple funny. I was already Six feet tall. By the end of eighth grade, I got pressured into playing basketball, but I was so meek that I usually just stood there while some terrifying girl shoved by me with the ball. I don't like to look at pictures of myself from that time standing next to other kids my age. I look like the teacher or like someone's off putting sister home from college. None of my pants fit correctly, and my socks were always pulled up too high. I used to listen to the song Eleanor Rigby in panic. In my interpretation, it was a song about how no one wanted to date poor old Eleanor Rigby, just like no one wanted to date me when I was 13. One day I was sitting by the gym after school with my friend Desiree when. When she told me, I picture you getting a boyfriend in college. She laid out this whole hypothetical where me and my future boyfriend reached for the same book at the library. At the time, I was offended. College. Other girls at my school, Desiree included, already had boyfriends. The middle school version of a boyfriend, where you were afraid to touch each other and broke up after a week. But still, I had to wait till college. But as it turned out, I did not get a boyfriend before college, nor in college, nor even for several years after college. And so I concluded the problem was not my circumstances. The problem was me. I was not dateable. After meeting me for the first time, people might say, oh, she was funny. But they'd never say, is she single? I was simply not a person that anyone could think of romantically. At college parties, boys would grab my friends and start dancing with them. And I would stay for a while, dancing alongside them like I was part of the good time. But eventually, I'd walk away. It was weird for me to keep standing there, smiling blankly at the wall while they were making out. By now, I'm in my 30s, and I actually do have a boyfriend. Sam and I have been together for four years. We live together. We've taken trips, know each other's moms, list each other on emergency contact forms. And yet still I can't shake this feeling that I'm behind, that there's something wrong with me, that I started too late and now I can never catch up. Sometimes Sam tells me stories about the girls he used to hook up with, or about his high school girlfriend or the girlfriend he lived with before he lived with me. I know that he's not trying to get back together with any of these people. I know he's as invested in our relationship as I am. Still, when he tells these stories, I feel so inadequate that I want to cry. A couple times I have cried and he's been confused and suddenly we're in an argument because I don't know how to explain why I'm crying. I want charming stories like that, want to rhapsodize about my past of young love and mutual discovery. Instead, my past is a wall I smiled at, and the only stories I have about people I've hooked up with are vaguely unsettling. To repeat, I liked life at a time before all that, back when it still felt like romance might happen for me, like any interaction could be the start of a love story for the ages. One time I brought whole food sushi for lunch and felt self conscious because I'd seen the Breakfast Club in which Molly Ringwald is mocked for bringing sushi for lunch. But Leif walked by my table and said is that sushi? And I said yes. And he said I love sushi. And I said Would you like a piece? And he said really? And I said yes and suddenly I was proud to have a lunch of whole food sushi. Leif talked constantly about a band called Billy Talent, a semi yelly alt rock group with lyrics about misery. I started listening to them because I knew Leif liked them and from there became an obsessive fan myself. Once I ran into Leif at a Billy Talent concert. I pretended not to see him because I didn't want him to think that I'd followed him there, but he came over and said hi to me. There were little moments where it almost seemed like he could be flirting with me. We followed each other on the blogging site Zanga, and for a while there was some sort of glitch where Leif was unable to comment on my page. When the glitch was fixed, he was so excited that he left me 100 comments in a row. Comment 42 said. On the 42nd day of Christmas, I gave to Kaylee 100 comments, lots of typing and a pear tree. I still have a journal from that time. In it I'd write Leif all these vague letters. It is humiliating to read these letters now to the point where I refuse to quote them here. Suffice it to say that I constantly referred to him as dearest. Surrounding the letters are my thoughts about myself, mostly how I wished I were a different person entirely, someone charismatic and sought after. Sometimes I'd have this huge swell of self hatred that I didn't know what to do with. Once I tried to cut myself, but the kitchen knife I chose was not very Sharp. And so it was harder than I thought it would be. And I gave up. When I find someone who wants to date me, I thought this feeling will go away. I hoped that Leif might be that someone. I'd concoct long fantasies about how we'd get together. And sometimes I'd realize what a good mood I was in. And then I'd realize the good mood was because of something I'd made up. Something that hadn't really happened at all. In the winter of eighth grade, I finally decided enough with the secret pining. It was time to let Leif know how I felt. And so I took action. And by took action, I mean that I delegated action to other people. There was a stairway right next to our classroom that was just a single flight enclosed by doors on each side. It was in this room of stairs that my friends Lucia and Emily cornered Leif and told him that I liked him while I ran home and hid. Afterwards, I asked them what he said. They told me he said okay. That night, in a fit of panic and despair, I got online, I logged on to Zanga, and I wrote a veiled, angsty post about what a huge mistake I'd made. Leif saw the post, as I knew he would, and he im'd my friend Karina about it. And here is where something amazing happened. Because in this conversation with Karina, Leif said he would date me. He said he thought I was cool. He was going to ask me out on Valentine's Day. Seeing couples perform how much they liked each other made me feel inferior. So I hated Valentine's Day with a showy passion. Each February 14th, I'd wear all black as a sign of protest. Leif's thought was that this romantic gesture might help me to reclaim the holiday. I know all this because at the time, Karina promptly copy and pasted the ims with life into an email for me. I couldn't believe what I was reading. I was so happy. Finally, I thought, finally, the thing that only happens to other people, it's now happening to me. On Valentine's Day, I got up and my mom drove me to school. People were giving out candy and paper hearts. I tried to look nonchalant. I went to science class, I went to lunch, to recess, to math, to basketball. And then school was over and I went home. Leif did not say a single word to me all day. I have no idea what happened or why he changed his mind.
Lucia
Huh? Did you ever talk to him about it?
Jonathan Goldstein
I rehash all this on the phone. With Lucia, Never did we speak directly about it. Like, we spoke through you and Emily, through Karina on IM and like, through my veiled zanga posts.
Lucia
Interesting.
Jonathan Goldstein
And having been my best friend for all these years, Lucia intuit's what I'm building up to. So you.
Lucia
You wanna try to find him or.
Jonathan Goldstein
Yeah, but I'm afraid I tried drafting a letter, and I was like, do I just sound indistinct? Anyway, so do you think this is completely insane to do?
Lucia
No, I mean, I'm sure you wrote. You're a very good writer and a thoughtful person, so I'm sure the way you approached it was good.
Jonathan Goldstein
Since Googling, Leif had always failed me, I turned to a public records database that I get through work. I was hoping to discover a possible mailing address for Leif, and I did. Looks like maybe he lives in Arizona. And I saw he had like a. From 2020. A court thing from defacing a political sign.
Lucia
Well, I guess you don't know which direction that I know.
Jonathan Goldstein
Yeah, I know.
Lucia
Hopefully it's a good direction.
Jonathan Goldstein
I want to talk to Leif directly, the way I never did back then. I want to know what he really thought of me and why he never asked me out on Valentine's Day. All these years, I've believed this story about how people don't see me romantically. But if I can change the beginning of that story, if I can see myself differently at 13, it could reframe everything that came after I name dropped you in the letter.
Lucia
She name dropped me because I'm so well known.
Jonathan Goldstein
Well, I was like, we used to live together, but now we both live with our boyfriends so that he wouldn't think I was, like, trying to date him now. Hi, Leif. I wrote in my letter. I don't know if you remember me, but we went to near north together. I had a huge crush on you, and I was hoping you'd be up to talk to me about what you remember from that time. I hang up the phone with Lucia and I walk to the mailbox. I send off my letter. But then several weeks go by and nothing. Did Leif get the letter and decide to ignore me, or do I just have the wrong address? Usually when reporting a story, I'd try calling at this point. And I did find a phone number for Leif. However, the idea of dialing it makes me want to lie down in the middle of the street and simply pass away. And so, just like I did at 13, I recruit someone else as an envoy.
Khalilah Holt
And who is that? Someone else?
Jonathan Goldstein
You. Oh, yeah, it's you.
Khalilah Holt
Okay, so I'm sort of like that whole quorum of girls all in one adult man.
Jonathan Goldstein
This is regular host of this program, Jonathan Goldstein. I want him to call Leif on my behalf to see if Leif got the letter and would be open to speaking with me.
Khalilah Holt
Yeah, no, I don't think that'll be awkward at all. Let me get my pattern down here.
Jonathan Goldstein
Oh, really? Hi.
Khalilah Holt
There was this girl. Her name was Kahlilah Holt.
Jonathan Goldstein
You should say Kaylee first. I think he would know me by Kayleigh.
Khalilah Holt
Hi, I'm Kaylee, Holt's boss.
Jonathan Goldstein
When you say it like that, it is really weird.
Khalilah Holt
That is weird. No. Hi. You don't know me, but I was enlisted by an old school chum of yours.
Jonathan Goldstein
Ew. Don't say school chum.
Khalilah Holt
An old flame.
Jonathan Goldstein
Ew.
Khalilah Holt
A paramour.
Jonathan Goldstein
My confidence is decreasing with every passing second.
Khalilah Holt
I won't embarrass you in front of your crush.
Jonathan Goldstein
Are you joking?
Khalilah Holt
Choking on this. Bon Bonus.
Jonathan Goldstein
As my boss asphyxiates on a piece of candy, I weigh the pros and cons of just making the call myself. But in the end, I make the same choice I did back then. Better to send an incompetent in my stead while I hide at home. I obsess all day Thursday. I obsess all day Friday. Jonathan doesn't offer me a single update. I can't even tell if he's made the call yet. Then the weekend begins, and I still have no idea what he's done. Okay, but whatever you did do, it worked because Friday night checked my email, and I had an email from Leif saying that he would talk to me.
Khalilah Holt
Wow. Okay. Well, let me just say I am almost 100% certain that I had nothing to do with that.
Jonathan Goldstein
Well, really? Because it happened that day.
Khalilah Holt
Yeah, it is suggestive.
Jonathan Goldstein
Jonathan tells me that he had indeed tried calling Leif's number.
Khalilah Holt
Okay, here's. Here's the call. You ready?
Jonathan Goldstein
Okay. Yeah.
Khalilah Holt
Okay. Hello, Is Leif there?
Jonathan Goldstein
Yes.
Khalilah Holt
Could I speak to him?
Jonathan Goldstein
Yes, this is her.
Khalilah Holt
This is Leif.
Lucia
Yes.
Khalilah Holt
Leif. I just want to make sure I have the right person. What is your middle name?
Jonathan Goldstein
Chicken Doodles.
Khalilah Holt
No, no, that isn't. That isn't the Leif that I'm looking for.
Jonathan Goldstein
I'm on the toilet right now.
Khalilah Holt
Okay. Is there anybody else in the house?
Jonathan Goldstein
In his email, Leif proposed that we talk in nine days, which is kind of a weirdly long time. I can't help but worry that he'll bail last minute that this will be just like Valentine's Day all over again. So in the meantime, hoping she might remember some clue about what happened back then, I text my old friend Karina, the one who brokered this whole Valentine's plan with Leif on im.
Karina
When you texted me that it was you, I was like, oh, my gosh.
Jonathan Goldstein
Like, did something happen? Like, is she calling me to say that Ms. Bergen died? Ms. Bergen being our longtime principal, which.
Karina
She did, by the way, if you didn't know.
Jonathan Goldstein
I did hear that. Yeah. Okay. May she rest in peace. I'd felt deranged texting Karina that I wanted to speak with her about Leif, a random kid from her eighth grade class. But Karina responded. I legitimately thought about you and Leif last week. So just like we used to in junior high, the two of us chat on the phone about a boy and then he. I am Ed. You shut up.
Karina
Did I send you the conversation?
Jonathan Goldstein
Yes. So then I. And buried in an old AOL account, I find that email from Karina with the whole conversation between her and Leif laid out.
Karina
I would like absolutely love to see it.
Jonathan Goldstein
Let me send it to you. Leif's screen name was Chaotic Detortion, which I think is just chaotic distortion spelled wrong. Okay, let me read this. Okay. At 10:17pm Nice. And as Karina reads here for you, dear listener, is a dramatic recreation of that I am exchange with two young actors playing the roles of Karina and Leif. Hey.
Leif
Hey, Leif. What's up?
Kaylee
Kaylee's talking.
Jonathan Goldstein
About what?
Kaylee
I think she is right on. Zanga.
Jonathan Goldstein
Hold on.
Leif
Let me see.
Jonathan Goldstein
Um.
Kaylee
Kayleigh likes me, right?
Leif
Did Lucia and Emily tell you something?
Kaylee
Yeah. After school the other day?
Leif
Yeah, she does.
Kaylee
Well, if she comes on, will you tell her something? Yeah, if she comes on, tell her that I'll go out with her. But my health is always screwing with my life, so I'm probably not going to be able to be 100% boyfriend material.
Jonathan Goldstein
Leif had some sort of illness the whole time I knew him, but I never knew how sick he was or what he was even sick with. He sometimes had to leave school early. He was on crutches for a while, and there were days when he just looked frail. But at 13, we didn't think to ask any questions back then. Karina just thought it was sweet he was considering his health in his role as my future boyfriend. Aw.
Leif
But do you like her?
Kaylee
This is kind of awkward. Yeah.
Jonathan Goldstein
All these years later. And that. Yeah, makes my heart start pounding. I was wrong. I think. See? I was wrong. He liked me. He said he liked me, but then it goes on.
Leif
Omg.
Kaylee
Don't tell her. I'm not crazy about her. But, hey, if she likes me, I don't hate her or anything. And Kaylee's cool.
Leif
Yeah, she is. So you want me to tell her that you'll go out with her? Why don't you just talk to her on Monday?
Kaylee
Do you think I should?
Leif
Yeah. Cause, I mean, I don't think she would believe me. And it would be nicer if you told her. Are you getting her something on V Day?
Kaylee
I guess. When is Valentine's Day next?
Leif
Next Tuesday. Omg. You should tell her on V Day. Cause she hates V Day.
Kaylee
Whoa. Yeah, I will.
Jonathan Goldstein
I always thought it was Leif who came up with the Valentine's Day plan, but it was actually Karina, it wasn't a romantic gesture at all. It was the gesture of a thoughtful friend.
Karina
But I don't remember anything after that. I didn't even remember that. He didn't end up saying anything. Like, he didn't end up saying anything to you at all?
Jonathan Goldstein
No. We never talked about it.
Karina
No, Kaylee, he did. I'm pretty sure he mentioned his health again. Maybe I followed up and he was like, honestly, my health just really isn't the best.
Jonathan Goldstein
So did Leif not ask me out simply because he was too ill? Was his not asking actually a romantic gesture? Something worthy of a Shakespearean tragedy? Or did he just not like me? I'd ask Slave to talk on Zoom, and I pray I won't break out or have a bad hair day because, you know, I want to look good. The morning of, I put on an eyeshadow that someone once told me was flattering and wear a T shirt for my favorite band because I figure it's cool to like music. Then I head to the studio and test the microphone. Hello. Hello. All right, that's working. I feel ill. I feel physically ill. Oh, my God. Okay, I can do this. Here we go. On the zoom camera, you can't even see my T shirt or flattering eyeshadow, so that was a lot of wasted effort. I see that Leif is in the waiting room. I press the admit button, and he appears on screen. Hi.
Leif
Hey.
Jonathan Goldstein
In spite of his deeper voice and tattoos, life seems the same. Like there's no discrepancy between the person I imagined all these years and the one I'm actually looking at. Um, how are you?
Leif
I'm great. I'm doing great. How are you?
Jonathan Goldstein
Doing? I'm doing. You know, unfortunately, faced with the person I imagined all these years, I suddenly can't remember how to have a conversation. It's like I've lost 20 years of social skills. Um, what. What, what's your life?
Leif
Um, my life? Well, I. Yeah, I don't know. I just do life things, you know, eat food, go to the grocery store. I've got a dog, you know.
Jonathan Goldstein
Sure.
Leif
What's your dog like?
Jonathan Goldstein
What's your dog's name?
Leif
Ronan.
Jonathan Goldstein
Good. Given that I'm incapable of asking any question more specific than what is your life? Or who is your dog? Leif takes the lead.
Leif
I've been doing, like, a lot of activisty stuff in Tucson, and that consumes more of my time than I probably should let it.
Jonathan Goldstein
In fact, the nine day delay Leif asked for was because of his activism. A few weeks earlier, he was at a protest with the Stop Cop City movement when he was tased and slammed against the ground by a police officer. He's been recovering from a concussion. At this point, we're 40 minutes into the conversation, and I've somehow managed to avoid asking Leif any questions about eighth grade at all. Even though he knows we're here to talk about how much I liked him, bringing up that time still makes me nervous. Um, what do you remember about me?
Leif
Yeah, I. I remember you being very tall and maybe a little awkward, but maybe that's just because of the crush or whatever.
Jonathan Goldstein
No, I was awkward. Yeah, yeah, yeah.
Leif
Like, I know that you told me at some point that you had a crush on me. I have like a vague memory of like, there was like that stairwell, Lucia telling me or something like that. Like, in the stairwell?
Jonathan Goldstein
Yeah. I ramble through my memories of what happened after that stairwell moment and finally up to the question that I really came here to ask. You were gonna ask me out on Valentine's Day, but then that never happened and I don't know why.
Leif
Oof. I'm sorry. Yeah, I don't remember. Like, the Zanga post sounds vaguely familiar.
Jonathan Goldstein
Can I send you? Because I in Fact have these IMs between you and Korrina.
Leif
No way.
Jonathan Goldstein
Can I email them to you?
Leif
Yeah, see what cringey ass things I have to say.
Jonathan Goldstein
Leif mostly reads through the IMs in silence, but at one point he makes a face and again goes oof. When he's done, he laughs self consciously.
Leif
All right, well, that was. That was. That was fun.
Jonathan Goldstein
Do you have no memory of this?
Leif
I don't know. Vaguely, I guess. Like, it's obviously, obviously it happened.
Jonathan Goldstein
I mean, yeah, it'd be weird if I typed all this up.
Leif
Yeah. Yeah, it'd be pretty weird.
Jonathan Goldstein
What part were you oofing at?
Leif
Oh, just. I mean, don't tell her. I'm not crazy about her, but, hey, you know, she likes me. It was just like that. Yikes. I don't really know what happened. Obviously, we didn't date. I don't. I don't think we did not date. Totally forgot about that.
Jonathan Goldstein
But, I mean, that would kind of be worse if we did date. And Yida, it just was gone from your memory.
Leif
Yeah, that'd be real shitty. Yeah.
Jonathan Goldstein
I mean, like, seems like you did not like me.
Leif
I do remember you being, like, very funny. But, yeah, I do agree, though. I think I wasn't into you.
Jonathan Goldstein
Into you, to use the 8th grade parlance. But then Leif raises a key thing. I've been wondering about the explanation that he gave to Karina at the time. His mysterious health issues.
Leif
I was, like, very, very, very sick. I was, like, in the process, essentially, of getting diagnosed with Crohn's disease.
Jonathan Goldstein
Crohn's is an autoimmune disease. Leif's intestine was attacking itself, making it hard for him to do basic things like walk or eat. In the years I knew him, though Leif didn't know he had Crohn's. He didn't know what was wrong with him. He was just getting worse and worse. It took over two years of waiting rooms and misdiagnoses before he finally got to a doctor who helped him. At that point, he was so sick that the doctor pulled his mom aside to say that she thought Leif might die. They immediately admitted him to the hospital, where he stayed for three months. I'm not a monster, so of course, I'd never say that I'm happy someone was so ill they almost died. But hearing all this, I can't help but feel kind of relieved. Because if Leif was that sick the whole time I knew him, then it wasn't about me not being good enough. There probably just wasn't any space in his brain for dating and crushes at all. So I put this to life.
Leif
I for sure had crushes.
Jonathan Goldstein
Well, there goes that theory. Can I ask who you had a crush on?
Leif
Yeah, yeah, I know I had a crush on Sorca for a while.
Jonathan Goldstein
I was gonna ask you that, actually. That's what I always suspected.
Leif
You got me figured out.
Jonathan Goldstein
Sarka had shown up at our school one year from Ireland, and all the guys instantly loved her somehow. In that one year, she dated three or four people. I, as someone who'd never dated anyone, found this profoundly unfair. Like, what about the rest of us? In my moments of insecurity, I always used to think there's no way Leif likes me, because I'm pretty sure he likes Sarka. So while on the one hand it's validating to hear that my Reid was right, on the other hand, it's devastating to hear that my Reid was right, I move on to my next theory. Do you think that any of it was height related? Uh.
Leif
I don't think so. I don't think so.
Jonathan Goldstein
So what was my problem? I asked Leif if I had some defect that prevented him from seeing me romantically. And although he really thinks about it, he can't come up with an answer.
Leif
I'm just trying to think if there has ever been anyone where, like, I'd love to date this person, but they've got this defect, you know, who he falls for?
Jonathan Goldstein
Leif says has always felt beyond words, especially in the eighth grade. Well, how. How do you feel about talking? Am I freaking you out?
Leif
No, not at all. It's fun to catch up and, like, hear what you remember.
Jonathan Goldstein
It's really nice to talk to you.
Leif
Yeah, you too, Kayleigh. Talk to you soon.
Jonathan Goldstein
All right. Talk to you soon. I'd felt good while I was talking to Leif. He was cool and nice as he'd always been. And yet, as soon as we hang up, I suddenly feel really sad. I sit there for a while, alone in the studio. And then, as I always have in times of stress.
Lucia
Hello, honey.
Jonathan Goldstein
I call my mom. I fill her in on the conversation and how the only logical conclusion seems to be that, yes, I was right. I am, in fact, undateable.
Lucia
Who wouldn't want to date you? You're awesome.
Jonathan Goldstein
Thanks.
Lucia
And I mean, I know I'm your mother, but that is also true.
Jonathan Goldstein
I feel like that's true in terms of, like, people wanting to, like, be my friend. But I don't feel like that's true for, like, dating.
Lucia
You feel it not just from when you were younger, but you feel it even now?
Jonathan Goldstein
Yeah.
Lucia
That makes me feel kind of sad.
Jonathan Goldstein
I'm sorry.
Lucia
Don't be sorry. It makes me feel kind of sad. And it makes me feel mad at people that don't see you.
Jonathan Goldstein
I don't. Yeah. I think I'm having a hard time characterizing it. Cause I do feel, like, weirdly emotional, but also, like, he was nice and the conversation was good, you know? So I don't want it to seem like I thought he was, like, being an asshole or anything. Like he wasn't.
Lucia
I don't hear that from you at all. I don't hear anything about any judgment about him.
Jonathan Goldstein
Yeah.
Lucia
You trying to piece it together for you?
Jonathan Goldstein
Yeah.
Lucia
Yeah. Give yourself a little space.
Jonathan Goldstein
I give myself several weeks of space. And then as I keep trying to piece it together, I decide there's one more person I want to speak with. Very excited to talk to you. So thanks for being up to do this weird thing.
Sarka
Yeah, no, it is weird, and I definitely feel weird about it.
Jonathan Goldstein
This is Serka, the Irish girl that Leif and the rest of the entire fucking class was into. Because in case it's not weird enough to reach out to my Crush after nearly 20 years, why not also reach out to my crush's crush? I always suspected he had a crush on you. And he said yes. Did you know that.
Sarka
Like, Jesus, like, he would, like, he would, like, burn CDs for me and stuff, Shoot out. I feel like he also gave me a sticker that said george W. Bush is a punk ass chump. So, like, yeah, I had an awareness.
Jonathan Goldstein
I want to talk to Sarca because I think of her as the anti me. Like, here's how Sarcas Valentine's Day went in junior high. She walked up to her boyfriend at the time holding a Hershey's Kiss and said, do you want this or do you want a real one? I want her to tell me how she achieved such romantic success. What she had that I didn't have. I had laid all this out in my initial message to her.
Sarka
So I said this to my husband, and he was kind of like, well, it's obvious, isn't it? Like, you were just new and different. And I think that's exactly it. Like, you guys had all been together from the age of two. Do you know? So I literally was just new and different. I honestly think it was that simple.
Jonathan Goldstein
I think that's part of it. But I feel like there was something about your personality too. Like, I feel like there was some, like, charisma or, like, confidence or. I don't know. I feel like.
Sarka
I think that that has got to be fake it till you make it, though, doesn't it? Because looking back and looking at the challenge that was laid at my doorstep, I probably just lent into some kind of confident Persona.
Jonathan Goldstein
Sarka only attended near north for a single year, and it wasn't an easy transition. Because of her mom's job, she was uprooted at 12 years old. And. And plopped down in a foreign country. Her dad, all her old friends stayed back in Ireland. She remembers the day she came to visit our school for the first time. And I remember crying and I remember.
Sarka
Saying, I don't want to go there. My memory isn't of feeling invincible or anything. Like quite the opposite. Like. Like overwhelming, shut down, you know.
Jonathan Goldstein
It's that sense of panic, Sarka thinks, that made her act so confident when she started school with us. It was her way of managing. Still, in the year I knew her, she often felt insecure. And dating didn't make that feeling go away. Any way you cut it. Boyfriend? No boyfriend. Junior high is hard. Circa tells me she's been married for about a year and a half now. How did you guys meet?
Sarka
We met on Tinder.
Jonathan Goldstein
I'd asked Leif the same question about how he met his partner.
Leif
Actually, through Tinder. We are a Tinder success story.
Jonathan Goldstein
I met my boyfriend through Tinder, too.
Leif
Nice.
Jonathan Goldstein
Sarika, Leif, me. Even though I always felt like they had some power I lacked, almost two decades later, we all ended up in the same place, living with people we met on Tinder. Back when I talked with my friend Karina, I'd asked her what her impression had been to me when we knew each other in junior high.
Karina
Oh my gosh, Kaylee, I adored you. I remember you being very intelligent. You were very funny. I know you were tall. Just, you know, at that age, I feel like you always look at everyone else and like, don't form your confidence or like, embrace every bit of yourself until later in life. And I remember being like, she has so many things going for her. Like, I hope that she becomes more confident.
Jonathan Goldstein
My past self was tall and awkward, and the boy I liked didn't like me. And all these years later, I'm still tall and still awkward. And I still often feel left behind by romance. But then again, the junior high me would never have had the courage to have these conversations at all. So maybe I did become more confident. And some people do want to date me. I'd want to date me. These days, I don't think too much about Valentine's Day. It turns out that I don't like being one of those performative couples any more than I liked watching those performative couples. This year. On February 14, my boyfriend made dinner. I did the dishes. Happy Tuesday, he said. Happy Tuesday, I said. Then we watched tv. It was nice, Sam. Now that the furniture's returning to its goodwill home, now that the last month's rent is scheming with the damaged deposit Take this moment to decide if we meant it if we trial or felt around for far too much from things that accidentally tied. Hello.
Anna Konkle
Hello.
Jonathan Goldstein
So, as promised, my conversation with Anna Konkle, co creator of Pen15. We talked about how emotional and viscerally bizarre it is to return to that middle school space again as an adult.
Anna Konkle
I mean, it was so humiliating.
Jonathan Goldstein
Yeah, like.
Anna Konkle
Like the first season especially, nobody knew what it was. The crew didn't know what it was. So people signed up to come on set and a lot of them haven't even read the script and they're like, what the fuck did I sign up for? Like, day one, Maya's in her bowl cup masturbating, like, okay, wait, we're really gonna try to play 13? Like, this is so embarrassing. And then being surrounded by the real kids and stepping on stage and be like, we're. You don't really think we are. We're we 30. The night before it came out, I just got on in like the fetal position on the floor and was like, this is so embarrassing.
Jonathan Goldstein
What did you do?
Anna Konkle
Like, what did you do? And you know what? The truth is, is it felt embarrassing for years after, actually. People would come up to me and say, like, I love it. And I'd be like, what are you doing today? Like, yeah, I couldn't hear it. It just. I felt so, so naked.
Jonathan Goldstein
How.
Anna Konkle
How was it for you making this versus when people started listening to it? Or have you had waves of this?
Jonathan Goldstein
Writing it and putting it together and like, playing it for people here was actually, like, positive. Like I felt like, oh, I'm really expressing what I felt and it's connecting with people.
Anna Konkle
Yes.
Jonathan Goldstein
And then I feel like once it was out in the world, it was a bit more of a mixed bag than I was expecting.
Anna Konkle
You mean how people felt?
Jonathan Goldstein
Yeah, like there were people who really connected with it, but there were a lot of people who hated it.
Khalilah Holt
Really?
Anna Konkle
I loved it. I mean, but obviously I'm gonna love it, I guess.
Jonathan Goldstein
I mean, that is something I was curious about, is I feel like there were people who just don't understand why middle school would be important or why you would want to think about it or go back to it. Like, have you run into that at all? Are there people who just don't think about it?
Anna Konkle
There's something about it that makes people really uneasy from the pitches of us first talking about it. So many men in particular actually like had to get up from a table or would be like, I'm getting nauseous, sorry. Hold on. Maybe it's like, physiological disassociation.
Jonathan Goldstein
Yeah.
Anna Konkle
That a lot of people can do.
Jonathan Goldstein
What was it like? Like, working with the kids. Like, do you feel like you had to translate to them, or did they kind of get it?
Anna Konkle
Most of the kids, when they're actually 13, aren't at an age that they're going, oh, yeah, I get why that would be. They're like, I didn't do that yesterday.
Jonathan Goldstein
Right. That's true.
Anna Konkle
You're just so in it. And even, like, seeing the Social Dynamics play out on set, that was very meta.
Jonathan Goldstein
There would.
Anna Konkle
I won't say who, but it would be like, oh, okay, he's the most popular and she's the most popular. Like, all the guys are texting her or whatever, and. And we always found the right kids. I thought the kids in your podcast were great.
Jonathan Goldstein
Thanks. That was my. My dad runs a community theater in Iowa, and he helped me cast those kids, so that was very sweet. Yeah.
Anna Konkle
Did you do community theater growing up?
Jonathan Goldstein
Yeah. I was never very good, but I. Because my dad, like, ran these, like, kids summer camps and stuff, I did always go, that's a lot of pressure.
Anna Konkle
For your dad to run it. And then, like, auditioning for your dad.
Jonathan Goldstein
Yeah. I think I wanted to be more of a. Like, a star because I wanted to be, like, close to my dad, you know?
Anna Konkle
But I relate to that, too. I remember going on, like, some work trip with him, and I remember, like, going to a pub, and they're being karaoke, and a girl went up and sang Nowhere man by the Beatles. And he was like, wow, she's incredible. He almost, like, cried, and he was clapping in a really intense way.
Jonathan Goldstein
Yeah.
Anna Konkle
I don't remember what song I sang next, but I sang a song, and I remember, like, finishing and, like, waiting for the same eyes and the same clap and being like, I'm right here, dad.
Jonathan Goldstein
Yeah.
Anna Konkle
And being like, no, that was good. It was a little pitchy. I had been estranged from my dad. I mean, this is another actually crazy layer to the whole show is like, I hadn't seen my dad in five years, but I'm, like, acting with the TV version of my dad and the one that I missed.
Jonathan Goldstein
Yeah.
Anna Konkle
And about a year before we started writing the last season, my dad and I had sort of been like, communicating more and trying to fix things, and. And then he called me and found out he had cancer.
Jonathan Goldstein
Oh, man.
Anna Konkle
And filming started.
Jonathan Goldstein
Whoa.
Anna Konkle
So I was, like, trying to, like, manage nurses and all these other things and be there as much as I possibly could. Flying back and forth and filming the show. But there were these scenes that were, like, overlapping with these huge moments where, like, my dad went to hospice and I had to go back to LA and film the scene where Curtis moves out of the house and gets an apartment and he has, like, a midlife crisis and gets this Sebring convertible.
Jonathan Goldstein
Yeah.
Anna Konkle
And were in the convertible. Like, the camera's right on us as we're driving at night with the top down and the air. The cold air blasting, which is, like, what my dad and I always did. And he had had that same Sebring, and we're having the talk about him moving out just as my dad's gone into hospice, like, moving out of the world, right?
Jonathan Goldstein
Yeah. Yeah.
Anna Konkle
And I just lost it. Talk about feeling like a kid as an adult. There was something about the extremeness of what we were trying to do, like, oh, we're building sets that look like our real houses.
Jonathan Goldstein
We're building.
Anna Konkle
It was like stepping into a memory.
Jonathan Goldstein
Were there particular scenes that were particularly intense to shoot, though? Definitely.
Anna Konkle
The first day of filming at my house, Anna Cones, you know, house I had given so many specifics about. It was nicer than my real house, probably, and. But, you know, my parents in real life divorced. They told me in seventh grade or eighth grade. And I've just had such a hard time accepting their divorce and walking in and seeing the house with, like, both of their things.
Jonathan Goldstein
Yeah.
Anna Konkle
Props and being, like, together. Like, the loon blanket that I described my dad having or the kind of lounger, you know, that he had that went to his apartment and what my mom got to keep, and it was like, it was all intermingled. And then on the bookshelves are all of these, like, half funny, half devastating pictures of me between two loving parents. And they're my, you know, set parents. So it was, like, silly, but I just wanted to cry. I was, like, going back to when. To the good times, you know, and it was a better version of the good times than what I had, really. We didn't have a lot of pictures, the three of us.
Jonathan Goldstein
I mean, like, after doing the show and, like, being in those moments again. Do you see anything in that time differently? Like, did it change your perspective at all?
Anna Konkle
I think it's interesting how people at that age have such different relationships with their own sexuality. Like that part in your podcast in the episode where the sort of popular girl goes up to the guy and gives him a Hershey kiss and says, like, what does she say?
Jonathan Goldstein
Do you want this or do you want A real one.
Anna Konkle
That's like the. I was. I. Like, I. I was like, well, I don't have that DNA.
Jonathan Goldstein
Yeah.
Anna Konkle
Like, I don't understand. And then she sort of went on to say, I think I created this Persona.
Jonathan Goldstein
Right.
Anna Konkle
But how much is that Persona, and how much is that just a different physical comfort? I was always, like, such a goody two shoes in that way, and, like, kind of known as a prude, and I was just not physically interested in guys like that. And if somehow they were, like, sensing. Cause my friends were more comfortable with that.
Jonathan Goldstein
Yeah, no, it's a good point. I think, similarly, I. I was not the most comfortable with it either. Like, I would have these infatuations with people, but to me, it just meant, like, we're gonna have this mental connection where we understand each other. Yeah, yeah, yeah.
Anna Konkle
Like, it was romantic.
Jonathan Goldstein
Yeah.
Anna Konkle
I remember when we first conceived of Pen and our agents or something being like, you need to add, like, character descriptions, and we just knew how we'd play them, but we hadn't been putting words to it. And that was one distinction that I finally was like, she's romantic.
Jonathan Goldstein
Do you remember what else you said in your character description? I'm like, I would find it so hard to have to, like, sum myself up in a character way, right? Yeah.
Anna Konkle
Yeah. I think, like, tall, bad posture. I think that I would have had the, like, hand over my stomach that I always did. Loyal to a fault. Friend probably, like, gets her identity from how much she admires Maya. And the fact that Maya admires her back gives Ana confidence.
Jonathan Goldstein
I mean, that's another thing I feel like you guys captured so well was just, like, the energy that having a friendship like that gives you, where you're, like, feeding on each other and amping each other up. Yeah.
Anna Konkle
That was the saddest part, I think, about it. Ending was, like, that innocence of friendship.
Jonathan Goldstein
Mm.
Anna Konkle
As actors and adult best friends of going, like, right now we get to live in this world where playing 13 is, like, you are just glued at the hip. And as you get older, you know, so many of us will lean on their romantic back to, you know, life. Back to your romantic partner.
Jonathan Goldstein
I feel like that's part of what's sad sometimes about being single as an adult is that everyone does lean so much on their partner, and you're like, wait, where am I now? I'm not anybody's number one. Because their number one is the person that they're. Yes. Like, yeah. Yeah.
Anna Konkle
I think it's something I've really struggled with to be honest in adulting.
Jonathan Goldstein
Yeah.
Anna Konkle
Is that expectation same? You know, I'm lucky that Maya and I think are a little bit aware of it and we will go to the Doctors with each other. Like, you know, there's things like. But I think it's not the norm.
Jonathan Goldstein
Thanks so much to Anna and to everyone who helped put this episode together. And for all my fellow Pen15 fans out there, you can listen to my full conversation with Anna if you subscribe to Put Pushkin Plus. I was very excited to get all this insight into making the show, and I don't want to hoard that insight from other Pen15 heads. So go to Pushkin FM plus to sign up. We'll be back next week with our final encore of the summer, and then the new season of heavyweight begins September 18th.
Anna Konkle
This is an I Heart podcast.
Heavyweight: Episode "2025 Update: Leif + A Conversation with Anna Konkle"
Release Date: July 17, 2025
In this compelling episode of Heavyweight, host Jonathan Goldstein undertakes a heartfelt journey to reconnect with Leif, a middle school crush who mysteriously vanished from his life at age 14. Alongside this personal quest, Jonathan engages in an insightful conversation with Anna Konkle, co-creator of the acclaimed show Pen15, delving into the emotional challenges of revisiting one's adolescent years as an adult.
Revisiting Old Flames
Jonathan begins by recounting his deep-seated crush on Leif during junior high. "[...] Leif was my crush, the object of my junior high obsession. I still Google him occasionally, but he's completely absent from the Internet" (03:04). Determined to find closure, Jonathan discovers a possible address for Leif in Arizona through a public records database, igniting hope and anxiety.
Enlisting Help
Unsure of how to approach Leif directly, Jonathan turns to Khalilah Holt for assistance. Together, they craft a plan to reach out, reflecting Jonathan's lingering insecurities and desire for answers about their unresolved past.
Memory Lane with Lucia
Jonathan shares nostalgic conversations with his friend Lucia, reminiscing about their shared memories of Leif. Lucia provides emotional support, affirming Jonathan's worth:
Lucia Holt: "No, I mean, I'm sure you wrote. You're a very good writer and a thoughtful person, so I'm sure the way you approached it was good." (15:08).
Uncovering the Past with Karina
Reaching out to Karina, another mutual friend, Jonathan uncovers old IM exchanges that reveal Leif's struggle with illness during their adolescent years. This discovery shifts Jonathan's perspective:
Jonathan Goldstein: "Leif had some sort of illness the whole time I knew him, but I never knew how sick he was or what he was even sick with." (31:36).
Reconnecting After Years
Jonathan finally connects with Leif via Zoom. The conversation is awkward yet sincere:
Despite the years that have passed, Jonathan finds comfort in Leif's familiar demeanor. However, the conversation leaves him with more questions than answers, particularly regarding why Leif never pursued a relationship on Valentine's Day.
Leif's Revelation
Leif reveals his battle with Crohn's disease, providing context to his past behavior:
Leif: "I was, like, very, very, very sick. I was, like, in the process, essentially, of getting diagnosed with Crohn's disease." (31:28).
This revelation alleviates some of Jonathan's feelings of inadequacy, as he realizes that Leif's lack of interest was influenced by his health struggles rather than personal rejection.
Emotional Aftermath
Post-conversation, Jonathan grapples with lingering self-doubt despite having a supportive boyfriend, Sam:
Jonathan Goldstein: "I am, in fact, undateable." (35:17).
His interactions with friends and family reveal a persistent struggle with self-esteem and the impact of unresolved adolescent experiences on his present relationships.
Behind the Scenes of Pen15
Transitioning to the second segment, Jonathan interviews Anna Konkle about her show Pen15, which artistically portrays middle school experiences through adult actresses. Anna discusses the emotional toll of recreating such a vulnerable period:
Anna Konkle: "I mean, it was so humiliating." (43:25).
Emotional Challenges
Anna shares the personal difficulties of acting as a younger version of herself, including dealing with her father's cancer diagnosis during production. The blend of personal trauma and professional responsibilities adds depth to her storytelling.
Parallel Journeys
Both Jonathan’s quest to reconnect with Leif and Anna’s experience creating Pen15 highlight the profound impact of adolescent experiences on adult life. They explore themes of memory, self-acceptance, and the complexities of revisiting formative years.
This episode of Heavyweight masterfully intertwines Jonathan Goldstein’s personal journey to find closure with a beloved childhood crush and Anna Konkle’s creative process behind Pen15. Through heartfelt storytelling and candid conversations, the episode underscores the enduring influence of our past on present identities and relationships.
Jonathan Goldstein: "For those who don't know the show, it is made by Anna Konkle and Maya Erskine, who are two real life best friends, and they play versions of themselves at 13." (01:12)
Lucia Holt: "He had this, like, light blonde hair that he dyed and was not like a long, like, down to your butt hair, long, like, like a bob length." (05:02)
Leif: "Do you know? So I literally was just new and different. I honestly think it was that simple." (37:16)
Karina: "I adored you. I remember you being very intelligent. You were very funny." (40:33)
Anna Konkle: "I was, like, trying to, like, manage nurses and all these other things and be there as much as I possibly could." (48:14)
This detailed summary captures the essence of the episode, highlighting the emotional depth and key discussions between the participants, supported by relevant quotes and timestamps for reference.