Sex + Love

First Kiss

Ten years after the fact, Jenny interviews the first boy she ever smooched.

first kiss

All images by Petra

When I was 15, I went around school in my mom’s old dresses and platform PVC combat boots that I had begged my parents to order for me from the Delia’s catalog. I wrote poetry about dying in the suburbs and was convinced there had never existed a teenager more misunderstood than me.

It was hardly a surprise when I became infatuated with my friend Chris’s older brother, Pete. He was two grades ahead of me, wore T-shirts that said “Fuck White Supremacy,” made me a mixtape titled “Punk Rock 101,” had friends who made zines about feminism and went to shows in the city, got me into Billy Bragg and Bikini Kill, quoted from The Dharma Bums before I had cracked open On the Road, had an encyclopedic knowledge of radical progressive movements when I was still trying to articulate why I was pro-choice, argued beautifully against the sanctions in Iraq, wrote impenetrable poetry that referenced Moby Dick, and sometimes gazed at me in a way that I described in my diary as “so intense I could DIE!!!!!”

The next year, Pete went away to college in the Bronx, and I started my junior year of high school even more crotchety and disenchanted than I was the year before. I started writing him long, painfully loving emails and assaulting him with my irresistible wit over late-night sessions of AOL Instant Messenger. Looking back over these emails, I’m pretty pleased to find that while there was a good amount of LOVE ME LOVE ME LOVE ME, I also wrote about stuff that really mattered to me. Like how starved I was for any kind of artistic/intellectual/creative action. How badly I wanted to be part of a community of people who inspired and challenged me. Or how in high school, it seemed like your only choices were to be either someone who was obsessed with getting perfect grades, or someone who didn’t give a shit. Where were the people who just wanted to learn new things and be exposed to everything there was? I wrote to him about my family and how they didn’t want me to write. I wrote about how badly I wanted to be a writer and how scared I was of finding out that I sucked big time.

At 16, while I believed I was interesting and funny, it seemed crazy that anyone else would. So when Pete came back to Long Island for the holidays and asked me if I wanted to meet him in front of the elementary school, I was shocked. I remember shakily waiting for my parents to go to sleep before sneaking out the back door, cutting through the woods behind my house, and running across the elementary school playground toward his car. Is it possible? I wondered as I sprinted across the grassy field. Can Pete possibly like me?

He was the first boy I ever like-liked and that night he became the first I ever kiss-kissed. Pete goes by Peter now. He’s a Ph.D. candidate in history, and I’m still writing poems about the boys I’ve loved and love. I caught up with him on the phone to ask him what he remembered about our first kiss. Ten years later and he’s still every bit the dreamboat he was in high school.

JENNY: Are you ready to do this?

PETER: I am.

JENNY: Can you tell me what you think you were like in high school?

PETER: Misunderstood is the word we all used, I think, looking back on it with some self-deprecation. Adolescence is an awkward time for anyone. I think after [I read James] Joyce I saw myself as Stephen Dedalus, like any romantic kid with literary aspirations. And I had tried and failed every sport known to man, so the arts seemed a natural refuge for my teenage misanthropy.

JENNY: Do you remember the first time you noticed me?

PETER: You were hanging out with Malgorzata. That was the first time I took notice of you physically. And because you were friends with Malgorzata, I thought you were probably a little different and that made me interested. I learned at some point that you were this literary genius who was the star of your class. So I was drawn to your tortured genius, of course.

JENNY: I don’t know about that…

PETER: Especially since I imagined myself as a quiet, tortured genius.

JENNY: Do you think I chased after you or do you think you chased after me or do you think there was mutual chasing happening?

PETER: I think we did like a Jordan Catalano–Angela Chase thing. We noticed each other.

JENNY: Do you remember anything about the first time we kissed? Where were we and what were we doing? I’m thinking it was at Prybil Beach.

PETER: Were we in the car when it happened or were we on the beach?

JENNY: I vaguely remember leaning against the hood of your car. But maybe I’m just openly fantasizing.

PETER: That was probably it … I remember you were very cutely shy about the kiss. You were a sweet kisser. You were … I don’t know how to describe it. You were …

JENNY: Gentle?

PETER: You were soft. You weren’t jumping on top of me or anything. It was more awkward than that.

JENNY: I don’t know if you know this, but earlier that same day, I had pecked another boy on the lips. It was this kid who had a crush on me in high school. We went to Morgan Park and very awkwardly embraced and he very awkwardly asked me to be his girlfriend and I just said yes because I was super passive back then. And then I came home and started chatting with you on AOL Instant Messenger or something, and you asked me if I wanted to go for a ride in your car, and I immediately messaged the boy I had embraced in the park earlier and was like, “Um, I’m calling this whole thing off. I just want to be friends,” and then dashed off to meet you. I think that was the same night we ended up kissing on the beach. I don’t know if I ever told you that.

PETER: You crushed this poor boy’s hopes and dreams.

JENNY: I was a jerk.

PETER: What a heartbreaker you were. Having your first kiss and leaving a trail of broken hearts behind you.

JENNY: Yeah, so calculating, already. How many times do you think we’ve kissed each other?

PETER: I don’t know … we did a lot of kissing.

JENNY: Just throw out a number.

PETER: Maybe a hundred times? How do we distinguish between one night and one kiss? I don’t know how we break that up mathematically. A lot of times.

JENNY: What do you do now? Do you think you are the person you thought you would be in high school?

PETER: Yeah, I think I turned out the way I expected. I have my self-criticism, of course. But I’m finishing a Ph.D., and hoping to use it to write. The road has been very unexpected and circuitous, and not without some regrets, but I think I’m generally about where I expected to end up.

JENNY: Is there a part of you that’s still the punk heartthrob I thought you were in high school?

PETER: Oh man. You know, I hope so. I’ve largely abandoned the music, beyond nostalgia—apologies to Kathleen Hanna—and I dress more bourgeois and suburban than I could have admired back then, but in social and political thought I’d like to think I’ve kept the rebelliousness against conformity and conservatism that first attracted me to that scene. The anti-conformists can also be just as herd-like and fashion-obsessed as the crowd … but I still light up like a kid on Christmas morning whenever I hear a Dead Kennedys song …

JENNY: What kind of lady do you think I’ve become since high school?

PETER: You turned out the way I had hoped you’d turn out. You’re still pursuing dreams, like I am, and that’s difficult to do. It takes a lot of courage. Neither of us is very bold or aggressive, but I think you’ve made a bold choice by trying to be a writer. And you’ve been really successful and kept at it. I like who you’ve become.

JENNY: That’s really sweet. [Dies a little bit inside with renewed love.] Do you think we’ll ever kiss again someday?

PETER: [Laughs] I don’t know. I don’t know. Anything could happen …

JENNY: All right. Thanks for answering all of my questions even though they were kind of embarrassing.

PETER: You’re very welcome. ♦


  • Amy Rose September 21st, 2011 3:20 PM

    i think i’m in love with both of these people? also, i am always surprised when someone’s first kiss-ee isn’t totally embarrassing, like mine was. fuck the white supremacy, swoon!

  • EveyMarrie September 21st, 2011 3:26 PM

    Awww that’s totally sweet :)

    My first kiss (and first love) was also with a punk kid. I was a freshman, he was a senior (friends with my brother :x whoopsie) and we dated for a few months. He always had the appearance that scared people away, but he was really a big soft teddy bear and had the saddest goddamn eyes anyone could have (had a really bad childhood)

    If I was still talking to him, I’d totally love to ask questions like that to him haha XD

  • Hunter September 21st, 2011 3:40 PM

    This was really cute.

  • Naomi Morris September 21st, 2011 3:42 PM

    Swoon. This was so cute.

  • Rita Unicornia September 21st, 2011 4:21 PM

    I’ve never been kissed :) I’m so happy they still remember!

    • back2thepast September 22nd, 2011 6:01 PM

      Ugh me either! I don’t wanna go throw myself at some random guy; I want it to be special. But I am getting impatient…. haha. One day! This is a cuuute story!! Love the photos :]

  • Pashupati September 21st, 2011 5:08 PM

    Are these nice pictures from a photoshoot, or a movie?
    Will there be other interviews on the same subjects? (or similar, or… whatever) Somehow, it’s endearing to read. Like watching a nostalgic movie.

  • mrselaine September 21st, 2011 5:10 PM

    loved this article..Jenny your writing is fantastic

  • Pashupati September 21st, 2011 5:10 PM

    Ah, wait. These are from a photoshoot, Petra being the person who made two of our photoshoots.
    And are the models impersonating Jenny and Pete? They look damn cool.

    • Jenny September 21st, 2011 6:35 PM

      I wish they were impersonating us! I was far, far, far more awkward than the beauties Petra photographed!

  • Mustachefan September 21st, 2011 5:25 PM

    AHHHHHH so cute.

  • sobrina September 21st, 2011 5:50 PM

    Oh my goodness, this is so dreamy!! I have a huge crush on Peter now and I want to be BFF with Jenny…

  • stephanie4786 September 21st, 2011 5:54 PM

    This was so endearing, I loved it!

  • PussyGalore September 21st, 2011 6:00 PM

    This is my favourite article yet.

  • garconniere September 21st, 2011 6:20 PM

    awwwww jenny this is so sweet. i love the photos they chose to pair with your story, and kind of swooned. i’m not going to lie, i’m a bit jealous. my first kiss was a total dink and i highly doubt it would be pleasant to re-visit those days.

  • jenjencm September 21st, 2011 6:58 PM

    Aaahh…I’m such a sucker when it comes to love. I’ve never had my first kiss yet. When I do I hope it turns out nice like Jenny’s.

  • HollyGolightly September 21st, 2011 7:18 PM

    I really enjoyed reading this. I loved the openness with which Jenny described such a personal phase and intimate moment in her life, and I loved the interview. I think we’d secretly all like to ask these questions to our crushes, boyfriends or girlfriends.

    My first kiss was very sweet, we had just shared a can of Fanta :-) Even though I was surrounded by my friends, who knew it was my first kiss and were cheering and clapping like a bunch of loonies, it still felt very pleasant and private.

    p.s. Jenny, I can’t wait till your poems are published!

  • kalika_ma September 21st, 2011 7:35 PM

    Great pictures!

  • Angie Bitchface September 21st, 2011 8:08 PM

    awwwww this is adorable! I wish my first kiss was as sweet as this one and with such an awesome person, instead of regrettable and with a jerk. your hopes and dreams at 16 are almost exactly like my hopes and dreams now. and I really love the photos!

  • diny September 21st, 2011 8:10 PM

    this is kind of first kiss stereotypes. sweet, cute, and shy. if i were Jenny, i’ll do something like this too. ask to my first-kiss-guy about our first kiss. kind of embarrassing, but it gonna make me know that time better (okay, i really wait for this first-kiss thing-y). i am in my teenage-angst-situation. many people said everything that is difficult for me now, not the most difficult thing in my life. 10 years later, i’ll realize that i am so silly to worry about small things. okay, i became so cheesy now.

  • LoversSaintsSailors September 21st, 2011 8:11 PM

    What an awesome article! The concept and the content. I loved it.

    I really hope you guys do more like this. I’d definitely be keen to read them.

  • unicorn September 21st, 2011 8:12 PM

    this is so sweet! i love this!

  • puffytoad September 21st, 2011 8:14 PM

    I’ve only kissed two people, and the first time I kissed each of them I laughed in their faces. I hope this trend does not continue…

  • Pyxie Gwynne September 21st, 2011 8:51 PM

    You had me at “mixtape.”

    But seriously, great article. And thank-you for pursuing writing! More people need to be courageous like you…even if it’s a “soft” courageous. This article is so insightful, taking us to a very personal moment in time and looking back on it…makes me nostalgic for first kisses and for high school Dead Kennedys loving literate punk boys.

    &can you please do more kissing with this guy who references the beginnings of your relationship as “… a Jordan Catalano–Angela Chase thing…” cute.

    (…i’m off to lurk the halls of the history bldg on my university campus…)

  • erin September 21st, 2011 11:04 PM

    :( I want my first kiss! Man, I just want a guy to like me… I’m pretty sure all the guys at my school most likely thing I’m too creepy to possibly like.

    • Jenny September 21st, 2011 11:49 PM

      You know what, Erin? I honestly thought the same thing when I was in high school. I was way shy and way weird and way awkward. But it turns out that all of those super trite platitudes about how there is someone for everyone are true. And sometimes the farther you get from high school, the more ‘someones’ you meet. Most of the boys in my high school were mean slobs, but the whole world is not mean slobs, I promise!

  • Bathsheba September 22nd, 2011 12:57 AM

    Oh man, that’s really good. I have crushes on them both.

  • lise_catz September 22nd, 2011 2:56 AM

    this made me happy

  • besty September 22nd, 2011 5:42 AM

    you guys are soooo on again for 2011

    (tv sitcom audience reaction) ‘woooooooooooooooooooo!’

  • samhatt September 22nd, 2011 8:24 AM

    “How badly I wanted to be part of a community of people who inspired and challenged me. Or how in high school, it seemed like your only choices were to be either someone who was obsessed with getting perfect grades, or someone who didn’t give a shit. Where were the people who just wanted to learn new things and be exposed to everything there was?”

    ^I feel like this perfectly explains how I feel. Whatever happened to going to school to absorb? I have friends but I feel like there is an endless list of things I’ll never be able to talk about with them. That is why I go on rookie mag almost every day : ) Thank you so much for writing these words, and of course awwww to the story :3

    • Halfaaperson May 19th, 2013 1:34 PM

      I feel the same! That quote stood out for me too. I’m lucky enough to have friends who I can talk to about things that interest me. Though it often takes a few drinks to get them to open up. (That sounds creepy. I don’t mean I intoxicate then so they talk to me), just that they seem to hold it all in until we get drunk then they really talk about how they feel.
      You should find a pen-pal. It’s really nice to just be able to rant to someone. Sending letters is pretty fun too as you can send it all on cute writing paper.

      Just remember to judge by your own standards and not anyone else’s. I struggle with worrying about grades and what people will think of me if I don’t have A* and that. It’s true people judge you and see you as less clever. People need to remember there’s a difference between being intelligent and educated.

  • Emma S. September 22nd, 2011 8:29 AM


  • Eline September 22nd, 2011 10:19 AM

    Aww Jenny this is so sweet and beautiful and almost idyllic (just like you are). I just wanted my first kiss to be over with, was an annoying teen with a dead mind and chose guys like I was, too. (No regrets though)

  • heartcity September 22nd, 2011 1:51 PM

    this made me swoon. i cant imagine interviewing the boy of my own first kiss, too many awkward feelings!

  • Ari September 22nd, 2011 7:11 PM

    He sounds dreamy :) haha this was cute

  • EdieSedgwick September 22nd, 2011 9:53 PM

    this is pretty cute.

  • ichewmylips September 22nd, 2011 9:53 PM

    this is such a sweet story! Pete sounds really amazing *sighs* Funny how we always remember our firsts for everything.

  • Laia September 22nd, 2011 11:32 PM

    this is almost TOO sweet & awesome for words. borderline magical.

  • alicekazam September 23rd, 2011 12:29 AM

    This was unbelievably sweet. I’m entirely jealous of the whole situation. Very romantic :)

    Unfortunately my first kiss was taken by a guy who decided I was too old to not have kissed anyone (totally untrue, but wevs). However all the kisses since then have been really lovely. Don’t worry girls!

  • onlyhaveeyesforyou September 23rd, 2011 2:05 AM

    I died a bit. You both should go out again, the whole article made my heart melt. He seems like such a respectable, and sincere person.

  • jeanette September 23rd, 2011 3:08 AM

    I love you both so much! What a beautiful thing to revisit. I sure would love to hear your poetry!

  • Peaches September 23rd, 2011 5:51 AM

    This is beautifully written. I love every moment of this article!! :-)

  • tinytractor September 23rd, 2011 1:02 PM

    Why does Jenny know my life?

  • reevsie September 23rd, 2011 1:41 PM

    this is written so lovely-ly !

  • rosestulipstiptoes September 23rd, 2011 4:25 PM

    So cute!!!

  • Gabby September 23rd, 2011 10:23 PM

    this just made me feel so warm and fuzzy inside!

  • cj575 September 24th, 2011 8:45 PM

    aww this was soo cute!! It’s crazy, but I’m still with my first kiss (like I’ve kissed others in between) but then started dating my ‘first kiss’ 3 years later!! Anything can happen!

  • Bean September 27th, 2011 2:22 PM

    I just want to say: hurray for the rebellious but kind punk rock boys!
    My favorite boy ever, or my boyfriend in real terms, is that boy. He was that boy when I met him in the seventh grade and he was that boy when he was my first kiss in the eight grade. He was also that boy when I broke up with him…. but, he was that boy when we got back together in the nineth grade! Haha. And he’s still that boy as a college in freshman. Like I said, he’s my favorite.

    • Jenny September 28th, 2011 1:37 AM

      Aw, that’s so sweet that you’ve known him since 7th grade! Here’s to kind punk rock boys everywhere! <3

  • bunny September 29th, 2011 2:54 AM

    I heard about the website on NPR and thought I’d check it out for my daughter. Found this terribly sweet story. Took me back to my first kiss, oh so many years ago, and sadly we weren’t romantic or sweet. I was 20 and never been kissed and met someone willing to kiss me. I realize now I really missed out on something, so to those of you desperately wanting that first kiss, please be patient and when the right one comes along you will know it and be very glad you didn’t rush it.

    • Halfaaperson May 19th, 2013 1:24 PM

      I’ll take note :) x

  • Halfaaperson May 19th, 2013 1:13 PM

    God I hope my first kiss is as lovely as that. And that I have the guts to peruse my dreams too. And I also hope it’s with a punk ;) it’s exciting to think of all the awesome things that await me in life. And the people. I’d love to be a writer too. But only my friends and family admire my work. I hope to one day expand my poetry and writing to the whole world!