In short
Heavyweight’s “2025 Update” follows Kalilah Holt revisiting her 13-year-old crush “Leif” decades later, then expands into a conversation with Pen15 co-creator Anna Konkle about returning to middle school and making Pen15.
Guests and backgrounds
Leif (a Tucson activist; recovering from a concussion after being tased at a Stop Cop City protest; later diagnosed with Crohn’s disease) and Anna Konkle (co-creator of Pen15 with Maya Erskine; plays a version of herself at 13; discusses production, casting real 13-year-olds, and personal family context).
Key claims
Leif says he did plan to date Kalilah on Valentine’s Day, but he was very sick and later forgot/doesn’t recall the Zanga/IM exchange; his “not asking” wasn’t rejection. The Valentine’s plan was brokered by Karina, not Leif. Crohn’s disease explains his inability to date. Pen15’s middle-school discomfort resonates physiologically and emotionally for viewers.
Notable examples
the stairwell confession; Zanga/IM “Chaotic Detortion” messages; Leif’s Crohn’s diagnosis timeline; Pen15 set scenes with real 13-year-olds; Anna’s father’s cancer/hospice overlapping with filming.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VORevisiting Middle School Memories
2:41 to 3:34
The host shares nostalgic stories about a childhood crush and the complexities of early love.
“This is Jacob Goldstein from Business History.”
Revisiting Middle School Memories
5:56 to 14:00
The host shares nostalgic stories about a childhood crush and the complexities of early love.
“From the ages of 12 to 14, Leif was my crush, the object of my junior high obsession.”
Reflecting on a Childhood Crush
14:00 to 17:49
The narrator recalls the complexities of her feelings for Leif during middle school.
“Suffice it to say that I constantly referred to him as dearest.”
Drafting the Letter to Leif
17:50 to 19:50
The narrator discusses her decision to reach out to Leif after many years.
“and I was like, do I just sound into same?”
Drafting the Letter to Leif
19:51 to 20:45
The narrator discusses her decision to reach out to Leif after many years.
“When we were kids, summer meant freedom.”
Waiting for a Response from Leif
21:04 to 22:02
The narrator anxiously awaits Leif's reply while reminiscing about their past.
“Availability, speed, and coverage varies.”
Waiting for a Response from Leif
22:07 to 28:00
The narrator anxiously awaits Leif's reply while reminiscing about their past.
“We also get to talk about his family life and playing the weekend chef.”
The Dramatic IM Exchange
28:00 to 30:45
Listeners will hear a dramatic recreation of an IM exchange between Karina and Leif, revealing teenage emotions and misunderstandings.
“And as Karina reads, here for you, dear listener, is a dramatic recreation of that IM exchange with two young actors playing the roles of Karina and Leif.”
Reflections on a Crush
30:45 to 34:24
Karina reflects on her crush on Leif and her memories of their interactions during middle school.
“Like, he didn't end up saying anything to you at all?”
The Health Challenge
34:24 to 37:15
Leif discusses his health struggles during their teenage years, revealing he was diagnosed with Crohn's disease.
“how much I liked him, bringing up that time still makes me nervous.”
Show all 18 chapters
Understanding the Past
37:15 to 38:35
Karina realizes that Leif's lack of romantic interest was influenced more by his illness than by her worth.
“I was, like, in the process, essentially, of getting diagnosed with Crohn's disease.”
Post-Conversation Reflections
38:35 to 40:44
After their conversation, Karina reflects on her feelings of sadness and the complexities of relationships.
“I know I had a crush on Sorka for a while.”
Reaching Out to an Old Crush
40:44 to 42:00
Karina decides to reach out to Serka, the girl Leif had a crush on, to explore her own feelings further.
“And then, as I always have in times of stress, Hello, honey.”
Reflecting on Junior High Relationships
42:00 to 48:00
Exploration of past crushes and perceptions of social dynamics during junior high.
“I don't hear anything about any judgment about him.”
The Anxiety of Adulting and Middle School Memories
48:00 to 48:56
Discussion about the emotional experiences of returning to middle school themes as adults.
“guitar solo Now that the last month's rent is scheming with the damaged deposit.”
Creating Pen15: A Unique Perspective
48:56 to 55:40
Anna Konkle shares insights on the challenges and realizations of making Pen15.
“So as promised, my conversation with Anna Conkle, co-creator of Pen15.”
Personal Reflections and Family Dynamics
55:40 to 56:00
Anna discusses her relationship with her father and how it affected her work on the show.
“And but, you know, my parents in real life divorced.”
Reflections on Youth and Friendship
56:00 to 1:00:18
Explore the complexities of adolescent relationships and adult friendships.
“version of the good times than what I had really.”
Transcript
Automatic transcript. May contain errors.0:06Pushkin.
0:10Hello. Hello. It seems like the spider has become the thing that catches the fly. You're welcoming me into the studio. Am I the fly? No, I guess you're the fly. I'm the spider. Feels pretty good. So, what? But yeah, as hopefully our listeners know by now if they're paying attention. Whoa, whoa, whoa. I was sensing a little attitude toward the listeners. Don't antagonize the listeners. That's rule number one in broadcasting. As our dear audience should know, we have been encoring some episodes this summer. And usually at the end, we'll have a little update with the guest about what's happened since.
0:55Yes. This is going to 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. Yeah, we talk about it. We talk about it, like, yeah, frequently, I would say. We do, yeah. When it was running, we talked about it a lot. I have to say it's probably one of my favorite shows, too. For those who don't know the show, it is made by Anna Conkle 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.
1:40For 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. 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.
2:18Yeah. So you guys end up talking about the episode and her show. And about just our respective middle school experiences. So let's get to listening, shall we? Let's get to listening.
2:37I'm Kalilah Holt, and this is Heavyweight. Today's episode, Laith.
2:51Right after the break.
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5:40Optum's also building technology that connects the whole healthcare system so it can better take care of the whole person, you. Optum is making healthcare work as one for everyone. See what Optum's up to at Optum.com. 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.
6:22I 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 creep.
6:58And 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 Laph 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. I remember him being kind of like wayfish almost, like kind of almost like ethereal. Crushes do not exist in a vacuum. They require gleeful gossip with your friends. And so I call Lucia, who's been my best friend since elementary school, to talk about our old classmate, Leif.
7:47He had this light blonde hair that he dyed. Not a long, down-tier hair, a long hat, like a bob length, but 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. But three of us huddled together on the scratchy Marriott comforter, stifling our giddiness as we dialed. Oh my gosh. I don't remember if we actually talked. The thing I remember is that we called. Did we talk to his parents? 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.
8:26Go upstairs and talk to him. Then she hung up on us. It turned out he had a sister named Emily. That's 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.
9:08Standing 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. 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.
9:38When I was 13, one day I was sitting by the gym after school with my friend Desiree 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.
10:19And 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.
11:03Sam 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.
11:55I 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.
12:17I liked Leif 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 Foods 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.
12:57I 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.
13:48I 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.
14:29When 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.
14:56In 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 onto Zanga, and I wrote a veiled, angsty post about what a huge mistake I'd made.
15:46Leif 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.
16:32I 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.
16:48On 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. Huh. Did you ever talk to him about it? 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. Interesting. And having been my best friend for all these years, Lucia intuits what I'm building up to.
17:44So you want to try to find him, or? Yeah, but I'm afraid I tried drafting a letter, and I was like, do I just sound into same? Anyway, so do you think this is completely insane to do? 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. 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 court thing from defacing a political sign.
18:32Well, I guess you don't know which direction that can go. I know. Hopefully it's a good direction. 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 letters. Name-dropped me because I'm so well known. Well, I was like, we used to live together, but now we both live with our boyfriend so that he wouldn't think I was, like, trying to date him now.
19:18Hi, 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.
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21:53Download the ChatGPT desktop app today and take on your most ambitious work. I'm Martha Stewart from the Martha Stewart Podcast. In this special episode brought to you by McCormick Signature Seasonings, I got to chat with Reddit founder Alexis Ohanian about his new venture, Retrieve Air. We also get to talk about his family life and playing the weekend chef. I'm a simple man. I use honey from the farm and I got my crepe. That's it. The girls like their Nutella. That's my breakfast ritual. I'm usually phoning in lunch a little bit because I'm really planning on a delightful dinner. The girls really like steak.
22:31I spoil them. So even if I'm doing kebabs, I'm using ribeye. I'm doing it right. Okay, well, please. Listen to the full episode of the Martha Stewart Podcast wherever you get your podcasts.
22:46I 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 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. And who is that someone else? You. Oh. Yeah, it's you. Okay, so I'm sort of like that whole quorum of girls all in one adult man. This is regular host of this program, Jonathan Goldstein.
23:33I want him to call Leif on my behalf to see if Leif got the letter and would be open to speaking with me. Yeah, no, I don't think that'll be awkward at all. Let me get my pattern down here. All right. Hi, there was this girl. Her name was Kalilah Holt. You should say Kaylee first. I think you would know me by Kaylee. Hi, I'm Kaylee Holt's boss. When you say it like that, it is really weird. That is weird. No. Hi, you don't know me, but I was enlisted by an old school chum of yours. Ew, don't say school chum. An old flame. Ew. A paramour. My confidence is decreasing with every passing second. I won't embarrass you in front of your crush.
24:15Are you choking? Choking on this bonbon. 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.
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24:39I 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.
25:10Wow. Okay. Well, let me just say, I am almost 100 % certain that I had nothing to do with that. Well, really, because it happened that day. Yeah, it is suggestive. Jonathan tells me that he had indeed tried calling Leif's number. Okay, here's the call. You ready? Okay, yeah. Okay.
25:35Hello, is Leif there? Yes. Could I speak to him? Yes, this is her. This is Leif? Yes.
25:51Leif, I just want to make sure I have the right person. What is your middle name?
26:00Chicken Doodles. No, no, that isn't the Leif that I'm looking for. I'm on the toilet right now. Okay, is there anybody else in the house?
26:22In 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. When you texted me that it was you, I was like, oh my gosh, did something happen? Is she calling me to say that Ms. Bergen died? Miss Bergen being our longtime principal. Which she did, by the way, if you didn't know.
27:04I 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'd you shut up did i send you the the conversation yes so that i and buried in an old aol account i find that email from karina with the whole conversation between her and life laid out i would like absolutely love to see let Let me send it to you. Leif's screen name was Chaotic Detortion, which I think is just chaotic distortion spelled wrong.
27:58Okay, let me read this. Okay, at 10, 17 p.m. Nice. And as Karina reads, here for you, dear listener, is a dramatic recreation of that IM exchange with two young actors playing the roles of Karina and Leif.
28:17Hey. Hey, Leif. What's up? Kaylee's talking about what I think she is, right? On Zanga? Hold on, let me see. Um. Kaylee likes me, right? Did Lucia and Emily tell you something? Yeah, after school the other day. Yeah, she does. 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.
28:54Leif 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, it's my future boyfriend. Aw, but do you like her? This is kind of awkward. Yeah.
29:32All 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. OMG. Don't tell her. I'm not crazy about her. But hey, if she likes me, I don't hate her or anything.
30:00And Kaylee's cool. 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? Do you think I should? Yeah, because 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? I guess. When is Valentine's Day? Next, next Tuesday. OMG, you should tell her on V-Day, because she hates V-Day. Whoa, yeah, I will. 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.
30:42But 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? No, we never talked about it. No, Kaylee, he did. I'm pretty sure he mentioned his health again. Maybe I, like, followed up and he was like, honestly, my health just, like, really isn't the best. 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?
31:29I'd asked Leif 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.
32:22On 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! Hey! 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? I'm great. I'm doing great. How are you 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's your life?
33:16Um 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 Sure What's your dog? I do a lot of like What's your dog's name? Ronan 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. I've been doing like a lot of activist-y stuff in Tucson, and that consumes more of my time than I probably should let it. 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.
34:10He'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 what do you remember about me yeah I uh I remember you being very tall and maybe a little awkward but maybe that's just because of the crush or whatever no I was awkward yeah yeah 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's like that stairwell Lucia's telling me or something like that like in the stairwell?
34:58Yeah. 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 going to ask me out on Valentine's Day, but then that never happened. And I don't know why. Oof. I'm sorry. Yeah. I don't remember. Like, the Zanga post sounds vaguely familiar. Can I send you, because I in fact have these IMs between you and Karina. No way. Can I email them to you? Yeah. See what cringey-ass things I have to say. 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.
35:53All right, well, that was fun. You have no memory of this? I don't know. Vaguely, I guess. Like, it's obviously, obviously it happened. I mean, yeah, it'd be weird if I typed all this up. Yeah. Yeah, it'd be pretty weird. What part were you oofing at? Oh, just, I mean, don't tell her. I'm not crazy about her, but hey, you know, she likes it. It was just like that. Yikes.
36:28I don't really know what happened. Obviously, we didn't date. I don't think. We did not date, no. I totally forgot about that. I mean, that would kind of be worse if we did date and it just was gone from your memory. Yeah, that'd be real shitty. Yeah. I mean, like, it seems like you did not like me. I do remember you being, like, very funny. But, yeah, I do agree, though. I think I, like, wasn't, like, into you, into you. To use the eighth grade parlance.
37:04But then, layphrases a key thing I've been wondering about. The explanation that he gave to Karina at the time. His mysterious health issues. I was, like, very, very, very sick. I was, like, in the process, essentially, of getting diagnosed with Crohn's disease. 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.
37:49At 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.
38:06I'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 Leif. I for sure had crushes. Well, there goes that theory. Can I ask who you had a crush on? Yeah, yeah. I know I had a crush on Sorka for a while. I was gonna ask you that, actually. That's what I always suspected. You got me figured out.
38:49Serka had shown up at her 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 Serka. So while on the one hand, it's validating to hear that my read was right, on the other hand, it's devastating to hear that my read was right, I move on to my next theory. Do you think that any of it was height-related?
39:32Uh, I don't think so. I don't think so. So what was my problem? I ask Leif if I had some defect that prevented him from seeing me romantically. And although he really thinks about it, Um, He can't come up with an answer. I'm just trying to think if, like, there has ever been anyone where I'm like, I'd love to date this person, but they've got this defect, you know? Who he falls for, Leif says, has always felt beyond words, especially in the eighth grade.
40:11Well, how do you feel about talking? Am I freaking you out? No, not at all. Okay. It's fun to catch up and, like, hear what you remember. It's really nice to talk to. Yeah, you too, Kaylee. Talk to you soon. All right, talk to you soon.
40:33I'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, Hello, honey. 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. Who wouldn't want to date you? You're awesome. Thanks. And I mean, I know I'm your mother, but that is also true. I feel like that's true in terms of people wanting to be my friend, but I don't feel like that's true for dating.
41:20You feel it not just from when you were younger, but you feel it even now? Yeah.
41:29That makes me feel kind of sad. I'm sorry. Don't be sorry. It makes me feel kind of sad and it makes me feel mad at people that don't see you.
41:49I don't, yeah, I think I'm having a hard time characterizing it because 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. I don't hear that from you at all. I don't hear anything about any judgment about him. It's you trying to piece it together for you. Yeah. Yeah, give yourself a little space.
42:21I 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. Yeah, no, it is weird. And I definitely feel weird about it. 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? um like jesus like he would like he would like burn cds for me and stuff you know i feel like he also gave me a sticker that said george w bush is a punk ass chump so like yeah probably i had an awareness i want to talk to circa because i think of her as the anti-me like here's how circa's Valentine's Day went in junior high.
43:28She 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. 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 I think that's part of it but I feel like there was something about your personality too like there I feel like there was some like charisma or like confidence or I don't know I feel like 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 in to some kind of confident persona.
44:29Serka 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 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 saying, I don't want to go there. My memory isn't of feeling invincible or anything. Like, quite the opposite. Like, like, overwhelmed and shut down, you know? It's that sense of panic, Sarka thinks, that made her act so confident when she started school with us.
45:12It 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
45:35Circa tells me she's been married For about a year and a half now How did you guys meet? We met on Tinder I'd ask Leif the same question, about how he met his partner. Actually, through Tinder, we are a Tinder success story. I met my boyfriend through Tinder, too. Nice. Serka, 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.
46:12Back 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. 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 I hope that she becomes more confident 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.
47:07But 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 14th, my boyfriend made dinner. I did the dishes. Happy Tuesday, he said. Happy Tuesday, I said. Then we watched TV. It was nice.
48:02guitar solo
48:30Now that the last month's rent is scheming with the damaged deposit. Take this moment to decide. If we meant it, if we tried. Or felt around for far too much. From things that accidentally touch.
48:56Hello. Hello. So as promised, my conversation with Anna Conkle, 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. I mean, it was so humiliating. Yeah. 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, OK, wait, we're really going to try to play 13? Like, this is so embarrassing.
49:35And then being surrounded by the real kids and stepping on stage and be like, we're you. We don't really think we are. We're 30. The night before it came out, I just got in like the fetal position on the floor and was like, this is so embarrassing. What did we do? Like, what did we do? And you know what? But 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? Yeah, I couldn't hear it. It just I felt so naked. How how was it for you making this versus when people started listening to it?
50:16Or have you had waves of this? 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. Yeah. 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. You mean how people felt? Yeah. Like there were people who really connected with it, but there were a lot of people who hated it. Really? I loved it. I mean, but obviously I'm going to love it, I guess. I mean, that is something I was curious about. 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.
50:55Like, have you run into that at all? Are there people who just don't think about it? 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. And maybe it's like physiological disassociation that a lot of people can do.
51:30What was it like working with the kids? Do you feel like you had to translate to them or did they kind of get it? 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. Right. That's true. So in it. And even like seeing the social dynamics play out on set, that was very meta. There would I won't say who, but it would be like, oh, OK, he's the most popular. He'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.
52:09Thanks. That was my my dad runs a community theater in Iowa and he helped me cast those kids. So that was very sweet. Yeah. Did you do community theater growing up? Yeah, I was never very good. But because my dad like ran these like kids summer camps and stuff, I did always go. That's a lot of pressure for your dad to run it and then like auditioning for your dad. I think I wanted to be more of a star because I wanted to be close to my dad. I relate to that too. I remember going on some work trip with him. And I remember going to a pub and there being karaoke. And a girl went up and sang Nowhere Man by The Beatles.
52:53And he was like, wow, she's incredible. He almost cried and he was clapping in a really intense way. Yeah. 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. Yeah. And being like, no, that was good. It was a little pitchy.
53:26I had been estranged from my dad. I mean, this is another actually crazy layer to the whole show. It's 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. Yeah. 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 then he called me and found out he had cancer. Oh, man. And filming started. Whoa. 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.
54:12But 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 L.A. 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. Yeah. And we're 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.
54:58Right. Yeah. Yeah. And I just lost it. Talk about feeling like a kid as an adult.
55:12There was something about the extremeness of what we were trying to do. Like, oh, we're building sets that look like our real houses. It was like stepping into a memory. Were there particular scenes that were particularly intense to shoot? Mm-hmm. Definitely the first day of filming at my house, Anna Cohn's 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.
56:00Yeah.
56:30version of the good times than what I had really. We didn't have a lot of pictures, the three of us. 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? I think it's interesting how people at that age have such different relationships with their own sexuality. Like that part in your podcast and 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? She said, do you want this or do you want a real one? That's like the, I was like, well, I don't have that DNA.
57:12Like, I don't understand. And then she sort of went on to say, I think I created this persona. Right. 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 because my friends were more comfortable with that yeah no it's a good point I think similarly 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 going to have this mental connection where we understand each other.
57:59Yeah. Yeah. Like it was romantic. Yeah. I remember when we first conceived of Penn and our agents or something being like, you need to add like character descriptions. And we just knew how we play them, but we hadn't been putting words to it. And that was one distinction that I finally was like, she's romantic. 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 like that yeah um I think like tall bad posture I think that I would have had the like hand over my stomach that I always did um 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 Anna confidence 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 that was the saddest part I think about it ending was like that innocence of friendship 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.
59:19And as you get older, you know, so many of us will lean on their romantic back to, you know, life, back to a romantic partner. 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 worth. Yes. Like, yeah, yeah. I think it's something I've really struggled with, to be honest, in adulting. Yeah. 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.
1:00:00Like, you know, there's things like, but I think it's not the norm.
1:00:17Thanks 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 Pushkin+. 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 slash 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.
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From the publisher
For our penultimate Heavyweight encore, we’re joined by Pen15 co-creator Anna Konkle to revisit last season’s junior high drama — #53: Leif.
On Valentine’s Day in junior high, Leif was supposed to ask Kalila out. But he never did. Leif’s lack of action that day impacted Kalila’s life to come. And so seventeen years later, she wants to know: what happened.
For more, head over to Pushkin+, where you can subscribe to hear an extended cut of Kalila’s conversation with Anna.
Credits
This episode was hosted and produced by senior producer Kalila Holt, along with Jonathan Goldstein and Phoebe Flanigan. The supervising producer is Stevie Lane. Production assistance from Mohini Madgavkar. Editorial guidance from Emily Condon. Special thanks to Max Green, Flora Lichtman, and Connor Sampson. In the IM recreation, Karina was played by Reagan Didier, and Leif was played by John Claassen — thanks to Greg Holt and Tony John for making that possible. The show was mixed by Bobby Lord. Music by Christine Fellows, John K Samson, Blue Dot Sessions, Katie Mullins, Florian Le Prisé, and Bobby Lord. Our theme song is by The Weakerthans courtesy of Epitaph Records.
See omnystudio.com/listener for privacy information.
