All My Exes: Part 5
A Season of Firsts
Writer and Producer: Evan Roberts
Story Editor: Kate Sullivan
Consulting Producer: David Boyer
Illustration: Andy Gottschalk
Table of Contents:
In high school, my ideas about 'falling in love' or being in a romantic relationship with a guy were purely theoretical.
My first year of college is when the rubber met the road.
Buckle up!
PART 5: First Time, The Devil & First Love
After I left home for college, it was a matter of weeks before I came face to face with another man’s penis.
A huge first.1
During a weekend visit to crash on a high school gal pal’s couch in New York City, I met FIRST TIME.
He was a regular visitor to her dorm suite of theater majors prone to spontaneous monologues and choreography.
But he was different.
Coy, observant, sincere.
Also known as kryptonite.
I was weak to his powers.
Feb 28, 1996
There is no respectable way to say one has had sex. So let’s just not say it since it’s quite obvious already.2
I’ll be ranking my journal entries on various sliding scales.
On the Catholic Guilt scale, this is an 8.
Our long distance affair consisted of hand-written letters, custom mix tapes, and hand-written letters that explained the reasoning behind each song on the mix tape.
There were so many letters, FIRST TIME likened our relationship to a “correspondence course.”
But in a matter of months, it ended because “I needed space.”3
I was 10,000% into him, but he was 300+ miles away.
The relationship was taking my focus away from my school assignments, and all the new people I was meeting.
Pause for Foreshadowing:
This was the beginning of a false binary that would impact future relationships.
There would often be a moment when I felt I had to choose between a boy and a personal goal.
I could have a relationship or I could pursue a dream version of my future self.
One or the other.
For most of my life, the boys lost.
A Season of Firsts, continued:
I smoked pot for the first time….
I shaved my head for the first time…4
A local queen put me in drag for the first time…5
…and in the spring I fell into my first Friendship with Benefits with a gorgeous horse-faced6 bisexual hippie from New Jersey.
I nicknamed him THE DEVIL at the time because I thought dating a bisexual was bad news for me.
But I couldn’t resist.
He was confident, relaxed and he paid attention to me. He did that boy thing where he made fun of me incessantly because he liked me.7 I was clueless about this flirting tactic.
I just thought he was a sexy jerk.
My situationship with THE DEVIL barely registers on the Ex-checklist, but he merits inclusion because he plays a pivotal role in another first: coming out.
A month after moving back home for the summer, I went out to see a movie (I Shot Andy Warhol) and returned home late at night to find an unfamiliar car parked in my parent’s driveway.
Inside, THE DEVIL was sitting on the couch with my mom watching TV.
Tongue, swallowed.
In no world had I ever imagined my mother sharing a couch with the organizer of my first threesome.
My mother was a hardcore Catholic back then: she got mail from Focus on the Family, a fundamentalist Christian organization; she taught me that ‘left is right, right is wrong’ when it comes to earring placement for men.
My dad voted for Reagan twice and owned a shotgun; he made one vaguely homophobic joke when I was in 7th grade that I never forgot.8
After a year of being very gay in college, I forced myself back in the closet to spare their feelings and our collective discomfort.
My vibe that summer was simmering rage, as I fully expected a “Love the Sinner, Hate the Sin” response if and when I did come out.
Sorry, mom, but I was planning on being a sinner.
When THE DEVIL and I said goodbye at the end of the semester, he took my “Maybe I’ll see you this summer” very literally.
He drove six hours with his hippie gal pal Emily without even fingering a landline.
My mother had fed them dinner and hung out with them all night - even though I had never ever mentioned his name to her before.
They crashed on my bedroom floor for the weekend and I called in sick to my job at the beach arcade.
Emily drove her Buick down sun-dappled country back roads while THE DEVIL and I made out in the back seat.
No seat belts.
My father caught wind that something was up.
That morning, he sat me down on his bed before he went into work.
“Son, are you a homosexual?”
THE DEVIL and I recall how it happened (includes a duck quack over his real name):
THE DEVIL went back to New Jersey. He sent a postcard.
In his wake, he left my parents with a newborn Baby Gay Activist. I ranted that they could expect a boyfriend to cross their threshold at any minute.
“I’m going to get a boyfriend, and I’m going to bring him over for dinner, and you’re going to be nice to him!” -Baby Gay Activist
I needed to prove to them that this was not a phase.
I worked at an arcade near the beach where the clientele and general populace was aggressively heterosexual.
I was out to myself but not to the rest of the world, so that summer I felt like I was an undercover sociologist in straight America.
July 16, 1996
All the men have hairy backs and beer guts. And all the women have tan lines from another bathing suit competing with the bathing suit they have on.
From 1 to the Great American Novel, this is a 6.5.
Mostly I was just a lonely navel-gazing gay boy with a journal.9
July 17, 1996
Dear Journal
I feel so hexed. Will I ever find someone who won’t mind my fleshy skinny body? My gullible inarticulate head? My messy face?
A solid 9 on a scale from 1 to “Aw, Poor Little Gay Boy.”
Then….
One day after writing the above entry, my friends J, L and I drove up to a gay youth group10 meeting in Concord, New Hampshire.
I spotted FIRST LOVE from across the room and was instantly smitten.
He was… perfect?
The youth group facilitator started an ice breaker that went around the circle.
Tell us your name, your age, and the liquid you would want to drown in.
Someone said cum.
A baby dyke said milk.
FIRST LOVE said: “Gatorade.”
Soon, J, L, me and FIRST LOVE were hanging out on the regular:
Late night dinners at Bickford’s on the Traffic Circle in Portsmouth, NH.
Watching Absolutely Fabulous stoned in an attic apartment in Ogunquit, ME.11
Driving up and down the Eastern seaboard with what we thought were mushrooms that we found on the ground in a baggie near the Bickford’s entrance.
Blockbuster called to remind J that his Absolutely Fabulous tapes were 9 days overdue. “And tomorrow they’ll be ten days over due, so don’t bother calling.”
After five days of hanging out in groups and sensing a quiet mutual interest, FIRST LOVE and I had our first kiss while standing in my childhood family room.
It felt radical to be kissing a boy in my parents house, directly underneath the room where they were sleeping.
Jesus wept. Mary fainted. I was in love.
July 23, 1996
Dear Journal,
I am in shock. It’s amazing when something you want suddenly happens to you.
He happened to me…. with his salmon GAP V-neck, green shorts, and brown Birkenstocks. Large loving eyes and rounded nose. Rose petal lips and chocolate skin.
On a scale from 1 to Hypnotized Gay Boy, this is a 10.
FIRST LOVE checked so many of my boxes for the perfect boyfriend, I created new boxes for him.
Smart. Confident. Stunningly Gorgeous.
Well-off. Well-dressed. Well-built.
And he drove what felt like a fancy car to me at the time.12
Inexplicably, he was head over heels in love with me.
I wasn’t any of those things.
I asked him to describe himself at the time we met:
Throughout the interview, his voice would trigger a visceral response in my body. His laugh unlocked memories I hadn’t thought of in decades.
The menu at the Chinese restaurant where we we regulars (sweet & sour pork)
The sound of his car blinker (very refined)
The smell of weed and musk (pheromones)
Anyways, the great thing about dating someone who had all the confidence in the world was that I absorbed some of it.
Even if it was only bravado.
Our summer romance was fun and sexy and I was learning about how to be with another guy, be vulnerable, and talk about my feelings.
I loved that I could be insecure or anxious and he wasn’t bothered.
“I’ll never break up with you,” he said.
Subsequently, the summer romance was set to the highest level possible.
Bound by Desire, our Hearts were Aflame.
Listen to me read FIRST LOVE this journal entry and his response:
EVAN: "Spending the day with him is such a beautiful thing. Rubbing legs at a Chinese restaurant, driving his car, feeding him rice, singing, meeting his cousin, sitting close to him in a booth at Bickford's, dancing slow at a lesbian club, holding hands on the highway. I want them to be in my life always. Everyday I grew more confident in our love and future and in myself. This whole thing is a dream come true. A gift from the God of chance. And when I tell him I love him, I mean it."
FIRST LOVE: “I just envisioned it just going on forever… So it was... it was a real shock to me when we broke up.”
Once we went back to school, things got more complicated.
His fraternity’s communal phone line was always busy.
He didn’t like sending long emails; I did.
He had a car; I didn’t.
We lived six hours away, had busy schedules and always had homework.
Cut off cold turkey from the daily fix of a perfect summer romance, I didn’t cope well.
I was emotional, depressed and obsessive.
He was all I could focus on.
And like with FIRST TIME, I saw myself pulling away from my friends and personal goals.
September 7
It rained the day he left. Everyone was sad to see him go - even the sky.
September 15
I am consumed by thoughts of him.
Sept 24
I’ve lost myself in him. I’m only secure when I’m around him. And even then, I doubt myself.
The Sad Obsessed Self-Loathing Gay Boy scale…
In January, we talked about having an open relationship. I’m not sure we even knew what that meant. We referred to it as “sexual freedom within monogamy.”
I made friends with another gay guy in my class. He was cute. He started to feel like a temptation.
Even though hooking up with this friend might not have been considered cheating, my self confidence wasn’t prepared to then let FIRST LOVE have sex with other people, too.
The idea of staying together or breaking up both felt unbearable.
Then, one weekend in February, FIRST LOVE drove out to visit for the last time.
FIRST LOVE: Do you remember what day that was? This I remember very well.
I had forgotten about the Happy Stupid Day sign, painted on a sheet of wood by a friend who had hated Valentine’s day ever since the injustice of a recent break up.
That night we got very stoned.
Later, FIRST LOVE and I stayed up talking in bed and I told him how hard the long distance was for me.
But, I don’t remember anything at all about what I said, how I said it, or his response.
All I know is that in the morning, FIRST LOVE was devastated.
After breakfast, he got back into his car and drove home.
FIRST LOVE: I understood why you did it because I can rationalize things quite well, but I guess it was such a surprise that I didn't see it coming. And it was on Valentine’s Day... I think you could have waited until the next time I had come for example, you know, when it wasn't Valentine's Day.
Feb 15
Dear Journal,
I’m feeling good now.
Breaking up with him was the right thing to do.
My reasons for breaking up were valid, and he agrees.
Which makes it easier for me.
I feel liberated. So right.
The “Really, Girl? Are You Actually OK?” scale…
I finally had room in my head for other thoughts.13
Now I could focus on my life.
But the relief didn’t last long.
The tempting new friend from my major? We hooked up and, no surprise, our sexual connection was different from what I was used to.
Lust instead of love.
I missed the familiarity of FIRST LOVE, his body, his smell, his “moves,” and the way it felt to be naked with him. And it was fading from my memory.
It’s not easy being the dumper.
You have to hold fast to the reasons why you wanted to end the relationship in the first place.
If you don’t make a list and read it every night, you are liable to be The Ex Who Keeps Calling.
March 30
Dear Journal,
Perhaps I should distance myself from FIRST LOVE. I don’t know if calling him does anything except make me miss being loved and wanted.
The ‘Insights You Will Never Listen To’ scale…
When you are lonely and all your friends are away for the summer and you’re a dramatic baby gay, you obsess about the times when life felt full.
I’ve had to reread a lot of cringe journal entries for this project.
The following entry might be the most self-aware thing I ever wrote in any journal.
May 4
Dear Journal
Perhaps I am jealous of him… and my attraction is born out of jealousy. His features, his body, his material wealth, his philosophical outlook, his peace of mind.
Now that I am no longer with him, I do not have his qualities. It’s this insecurity that I bring to relationships and that screws them up.
I broke up with him to regain myself, only to learn that I don’t want to be with myself. I want to be someone else.
I’m wondering if all my relationships are doomed to fail until I am secure with what I have, where I came from, and what I look like.
On a scale from 1 to Miss Cleo…
That summer, I kept trying to woo FIRST LOVE back.
Can you believe I asked if he would drive out for a visit??
But in late July, a year after we first met at the gay youth group in Concord, NH, he said the final words:
He didn’t want to get back together.
July 22
Dear Journal,
First Love, you are dead to me now. Only a memory. A wadded up tissue after sex left under the bed.
I didn’t expect he wouldn’t want to get back together again.
I can’t bear the thought of him in love with another boy.
And I can’t fathom who I will fall for next, if there will be a next.
July 23
Dear Journal,
I can’t wait until love songs stop being so poignant.14
The Drama Queen scale…
During the THC-infused summer after my sophomore year of college, I recorded conversations with a handheld cassette recorder.
I would place it in the middle of a group of friends hanging out… and it’d easily get lost on a coffee table of ashtrays, bong water and Chinese take out.
The following archival cassette captures me and friends on a summer evening, stoned and relaxing on a grassy knoll and taking stock of our summer flings.
I had just decided to move back in with my parents, find a job and save money for my last two years of college elsewhere.
EVAN: He was perfect, he was the most perfect boy I’ll ever be with. And like, I’m wondering if fucked up this situation because I broke up with him…
EVAN: Am I talking about ex-boyfriend things too much?
JEN: It possibly could be.
But I kept talking about ex-boyfriend things.
EVAN: After the first love, it’s kind of tainted, you know, love is never the same…
When I first heard this recording, I thought, “Shit. I sound so young and immature.”
The idea that after FIRST LOVE, love in general was tainted and never the same?
That’s a little silly, since - spoiler alert - I continued falling in love for many years. There were second and third loves.
But then I remembered what it was like to be 19 and I realized there was truth to what I was saying.
Falling in love was never the same after FIRST LOVE, because now I knew what it felt like to break up with someone and still love them.
In every relationship after this one, the feeling of being in love would always coexist with the fear of losing it.
The next time I saw FIRST LOVE in person was two years after we broke up, at a July 4th dinner with mutual friends.
I had my cassette recorder and taped him driving me back to where I had left my car a few towns over.
I was frustrated. Our conversation felt superficial.
I realized my access to him was now limited.
In the below audio clip, you won’t hear us talk about anything interesting.
He tells me about what he does when he has to take a piss on the highway.
And then he says “It was so nice seeing J,” our mutual friend. And that “he looks really good.”
In the silence that follows, I can hear myself seething.
I wanted more. But I wasn’t ever going to get it.15
He dropped me off at my car and we hugged casually over an empty iced coffee left in the console, the plastic straw digging into my T-shirt.
It was an anti-climactic goodbye.
A minute later we both stopped at the same gas station and I watched him from afar as he pumped gas into his car.
Then I sat behind him in traffic as we waited to get on the highway.
July 4.
Dear Journal
With the flick of my high beams, I let him go in front of me, allowing him to squeeze past and go through a yellow light and leaving me with the red.
He goes north, I go south.
Strange how it can start and end in the same boring old town.
On the scale from 1 to “Lucinda Williams Singing “Out of Touch”…16
It would be ten years after our breakup until FIRST LOVE would have his next relationship.
He was living back on the island where he grew up, and dating a local bisexual man. They would walk around town holdings hands and everyone in the small island community was aware of their relationship. But his parents and the boyfriends parents did not like them together.
So his parents conspired with the boyfriends parents to send him away. The boyfriend had never gone to college, so they paid for his full tuition at a school in America.
One morning, FIRST LOVE woke up and all traces of his boyfriend were gone. He was sick for four days.
“That's when I realized that you could get physically sick from a broken heart,” he said.
FIRST LOVE moved to Europe, and became a teacher. At the time of our interview, he had not dated anyone since.
He said he was happiest alone and had no desire to be in a relationship or to share his life with someone.
FIRST LOVE: I’m happiest when I'm just by myself, which is weird, I know, but I guess whatever makes me happy. Whatever makes you feel the best.
EVAN: That's what you should do.
FIRST LOVE: Exactly. And that's what I'm coming to terms with. Um, I must admit, I wonder when I'm 70 years old or 80 years old… am I still going to be happy just being by myself? And that's a question I'm not gonna be able to answer until then.
I started to feel horrible.
I was one of two major relationships in someone’s life, and in both cases, the break up sideswipes him from out of the blue.
Did I help traumatize this man for life?
FIRST LOVE said that wasn’t true. He’s just the kind of person who is more comfortable by himself, he said.
FIRST LOVE: It's less “I've been hurt in the past,” then it is, “I just like being by myself.”
…It may be a combination of the two… but it's not like I have some kind of trauma.
And for a few years, that’s where the story ended.
EPILOGUE
Initially, ALL MY EXES was going to be a podcast, with each episode devoted to one or two people.
I began with the FIRST LOVE relationship story, and edited a 30-minute rough draft.
But the tone wasn’t quite right, and I moved on from that iteration of the project.
In 2021, I was in Europe for a month, and was able to visit FIRST LOVE at his home. It had been over 20 years since we saw each other in the flesh.
On my last night, I played him the 30 minute rough draft.17
We sat in his living room as the sun went down and I recorded his thoughts on my phone after we finished.
FIRST LOVE: That was really beautiful. Like from the very beginning, even before you started talking about “us”, I got emotional.
…It's really emotional to hear parts about your story that I did not know, and how you felt, especially after we had broken up. The recordings of you talking about me, like that make me kind of sad…
He continued:
FIRST LOVE: It's really emotional to hear someone else tell my story because I've always told my story. What you pieced together for me… like after I broke up with you, I wasn't with anyone for a long time, because it took me a while to allow myself to get back in the situation. And then when I got in that situation, it ended badly again, and I haven't had anyone since. So it's like strike one, strike two, I guess. {laughs} And, I haven't really gone for strike three. Is that weird, or wrong or - what is that, do you think?
EVAN: What is that do I think…? I don't know. Cause it's your life and you are happy alone. I'm here in your house. You are happy and you have a lovely place and you're, you're content.
I asked if he was avoiding relationships to avoid getting hurt again.
His response, reflecting how his view of romantic love had evolved, perfectly embodied the themes I want All My Exes to capture.
EVAN: Are you good because you don't want to be hurt again, like in the last relationships?
FIRST LOVE: No. At this point, if I were to be with someone, I would not get hurt because I'm not gonna fall in love. You know what I mean? If I meet someone, I will be someone who I have a lot in common with. We would do things together. We would love each other, but I wouldn't be head over heels in love. I'm not certain of anything, but I'm pretty sure that I'm not able to ever feel that kind of love again.
EVAN: I totally understand. Like the the crazy love that we had when we were 19 and 21 is because we were young and not experienced.
FIRST LOVE: So the kind of love that's gonna make me like completely heartbroken - that no longer exists in me. There's another kind of love in me that's probably as much love. Like I could love someone as much, but not in the way that is going to allow me to get that hurt.
The 19-year-old me heard this and felt both remorse and guilt.
“I’m not able to ever feel that kind of love again” is the worst sentence in the world to have helped make possible.
Now, in my 40s, with a lot more experience and 16+ exes to prove it, I know that ‘that kind of love’ is an immature kind of love.
Unweathered. Unsteady.
Since then, we’ve been weathered and we’ve moved to sturdier ground on our own.
It felt humbling, lucky and good to have the opportunity to revisit the memory of that kind of love, if only for a weekend.
One week after my visit, FIRST LOVE met his next boyfriend.
They’ve been dating for over two years and live together.
The next chapter leaves behind my teen years and rolls around in my Messy 20s, taking us further into the dating life of a young gay man whose frontal cortex had not yet fully developed.
Tune in for Part 6 where you’ll hear:
Next time on….
I’d love to hear your thoughts about this series and your own stories about exes.
Leave a comment below!
This is not a pun!
Tell me you were brought up Catholic without telling me you were brought up Catholic.
Breaking up with your long distance boyfriend on your dorm room landline? So anti-climactic. Do not recommend.
Everyone said I looked like Billy Corgan from the Smashing Pumpkins, which didn’t feel like a compliment at the time.
As I fitted the wig around my head for the first time, she exclaimed “OMG, you look just like my cousin Angela!”
This is a compliment!
One time, I lost my tweezers that I would use to pluck my uni brow hairs. So instead, I shaved the hair between my eyebrows with a Bic razor and I guess the result was quite obvious. He was the first to notice and always brought it up.
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I absolutely adore my mom and dad; They are two of my favorite people in the world. At the time of this story, it felt we were on opposite sides.
Not much has changed.
Seacoast Outright probably saved my life.
Nissan Pathfinder.
…about myself, as the portrait illustrates.
The most popular song of the summer was “I’ll be Missing You” by Puff Daddy.
A core frustration for me with exes that partly inspired me to create this project.
Perhaps something I will share at a later date…