Writer and Producer: Evan Roberts
Story Editor: Kate Sullivan
Consulting Producer: David Boyer
Illustration: Andy Gottschalk
Table of Contents:
Part 6: MESSY 20s
DELUSIONS
As a kid, I was raised on fairy tales and absorbed their messages uncritically (see above).
By the time I starting dating as an adult, I knew real life relationships would be more complicated than Love at First Sight + Happily Ever After. But I also left room for the possibility that some of that stuff might actually come true for me.
Maybe I’d be lucky.
My catnip were those RomCom climaxes where the cute but previously emotionally unavailable guy acknowledges his deep and abiding love for you— and in fact he’s always loved you, etc. etc.
My brain had yet to reach structural maturity and I was a very impressionable, moody, angsty little gay boy who just wanted a boy (who everyone else thought was desirable) to desire me. 💁♂️
That person was out there—and you better believe I theorized about it in my journal.
Dec 1992
Dear Journal,
I believe in soulmates and that you are made for another person.
I wonder if my wife1 is thinking about me right now? (hi honey!)
After serving (in all ways) as an altar boy at church, I learned in Sunday school that God had a plan for me.
I was comforted by the idea that I was “destined” for something—or someone.
I was hooked by the pilot episode of Dharma & Greg, where the eponymous characters cross paths as children in the subway and then again as adults.
EVAN: I was thinking the other day about who I'm gonna fall in love with… I don’t know. I could be a bachelor for the rest of my life. But I mean, I don't know if that's true. I mean, I really wanna find like, you know, Dharma and Greg, you know, find someone on the subway2…
Where was my Greg?!3
The Messy 20s was all about chasing the fantasy of the perfect guy, the perfect connection, the perfect relationship.
In this chapter, I’ll lose myself in a passionate but star-crossed affair with LEO LOVER and then later mess up my chance at a stable long-term relationship with MR. CLEAN.
We’ll also take a Walk of Shame down Memory Lane and visit the Messy 20s Hall of Fame Archive.
Dear reader, get ready for a messy decade of redefining what it means to be in love.
November 5, 2005
Dear Journal,
Love is a new idea. My definition keeps getting revised.
FIRST LOVE started it all, but since then it’s been amended over and over and over….
LEO LOVER
My junior year of college, I was home for Christmas break for six weeks. The perfect amount of time for a holiday fling.
In the mood for love, I went to see the latest romance in theaters and was immediately triggered.
December 25, 1998
Dear Journal,
After seeing “Shakespeare in Love,” I tried to envision myself falling in rapturous love like Gwyneth and I couldn't.
Perhaps I inherited the bachelor gene from my uncle, the loner who is strangely happy that way.
Almost two years after dumping my last boyfriend on Valentine’s Day, I was lamenting at the very real possibility that I would never experience another passionate love affair.
I picked up a temporary holiday job at the cafe in Barnes & Noble, and was definitely not doing whippets in the back when it was slow.
One night, I was coming down the escalator at the end of my break when I saw him being trained at the registers.
He was the most beautiful man I had ever seen.
Chiseled jaw, huge lips, broad smile. The swagger of a triple Leo.
Perfect.
He grew up in South America but was now living with his family in New Hampshire. For a 22 year-old, he’d already had a long and twisty life story. He could read people and had the street smarts of someone who had to grow up fast.
He knew a lot about astrology, hence his name here. Like a typical Leo, he emanated a warm masculine sexuality, but could also be playful and goofy. I loved his big generous laugh.
He was the Romeo to my Juliette Lewis.
Dec 27, 1998
Dear Journal,
I dropped him off at his place. After an uncomfortable silence he said “I haven’t said this to anyone in three years, but I really like you. A lot. And I would like to kiss you.”
I said I felt the same way. And then we kissed and it was magic….
He even likes the Cowboy Junkie’s “Sweet Jane”.
The kiss was incredible, but I was also wary of repeating my experience with the last boyfriend, and how easily I focused 100% of my energies on a boy and forgot about myself and my own life.
Further down the page I wrote:
…I would like to state here and now that my autonomy is now my new project. I know my tendencies where it comes to boys I like a lot, and boys who like me a lot. I must remain alive and whole.
Keep reading to see how long my autonomy was my new project.
The next day at work, we had to pretend our kiss never happened. LEO LOVER was afraid of jeopardizing his new status as a manger. I was having trouble with this public deception, already letting myself get swept up in the fantasy.
Dec 28
Dear Journal,
The secrecy is a uncomfortable. I understand his concern. But the silence and fleeting glances tainted the bare and emotionally naked planes that we uncovered the night before.
He says I can tell him anything. And I say things like, "I have fallen…” or “You make me intensely happy” and afterwards I feel I have said too much. Hmm. Perhaps I am expecting too much from him already.
This was written one day after my Declaration of Autonomy.
But it makes sense. I wanted to be wanted. And when I got it, I wanted more.
My holiday break was like a six week honeymoon where I avoided my family and responsibilities and spent my time with him drinking, smoking and renting cheap hotel rooms just to be able to wake up next to each other.
I vacillated from being realistic, to being totally bat shit crazy.
January 3
Dear Journal,
I wish we weren’t doomed to part in two weeks. Who knows what will develop between us that might be cut at the thick of the branch right as the flower is blooming?
This whole being in love thing is fun, but I can’t glamorize it. I can’t start thinking like a romantic. I want to devote so much to him, but at this point in my life, I can’t. I’m in a different world when I’m with him. It’s not reality. I don’t know him very well at all, and yet I’m planning my life with him!
Jesus, I just talked to him on the phone and his voice gives me an erection.
Late one night in January, LEO LOVER and I impulsively decided to drive to a bar 90 minutes away in Portland, Maine. We drank so much at the bar, we passed out in his car until the early morning.
LEO LOVER: Now the only thing is they close at 1 o'clock. They don't close late, like they told me. So, we're gonna be there for like an hour.
EVAN: That's cool.
LEO LOVER: But there's an after hours club next door to that one. And it's open until 3:30 in the morning. So, after we get all drunk, we'll decide whether we want to go to or not.
EVAN: Okay.
LEO LOVER: We'll play it by our rules, baby. Our rules. [animal noises] We're so queer!
The closer we got to my late departure date, the more the romance heightened.
We started to talk about the future and maybe living and working on Martha’s Vineyard that summer.
But the day came when I left for my second semester in London, and I found myself back in a long distance relationship— the second one in a row.
I fell into the same trap as the year before: obsessing about a boy when I should have been focused on school work. I spent a lot of money on phone cards and hanging out in phone booth at the youth hostel where I lived.
We broke up amicably in mid-March but still talked sometimes on the phone.
When I returned back home in June, I was ready to start dating again. But then he revealed something that at the time felt like a betrayal, and we broke up for good.
Dear Journal
June 29, 1999
LEO LOVER is destructive. Our friendship will fade. Passion can not translate itself into anything less than itself.
That summer, I remember thumbing through astrology books at bookstores to learn more about Leos. I wondered if I should ever date another Leo again.
We didn’t talk for four years. Then, one day I got a call on my cell phone from an unknown number. He had called to apologize.
And over the years, we became friends again.
I met with LEO LOVER at his home in Los Angeles. It had been a decade since we saw each other in person.
His husband was away on business in San Diego, but had left us some whiskey to drink for the interview.
LEO LOVER: Me cheating on you was fucked up, but there was nothing that I could have done not to have had that outcome in the situation that I was in. There was no way I could have kept up with that relationship based on my life situation, the long distance thing, and the stark contrast between the life you were living in the one that I was, you know what I mean?
EVAN: I do now. I can't imagine why we would ever have decided to stay together. I mean, we had a passionate affair, but we didn't just keep it like that. We decided to put rules or expectations on it..
LEO LOVER: And commitment…
At the time, I did not see the parallels to my last long distance relationship with FIRST LOVE, and could not imagine an option for a long distance relationship that wasn’t monogamous.
EVAN: Yeah. And maybe it would have survived, had I not grown up in such a like Catholic place and had been more experienced. Maybe we would have survived a bit longer and been a bit more open and fine with whatever happened while, while we were apart.
LEO LOVER: Yeah. But that's sort of… you can't have one without the other. There was a purity about the emotions that we were feeling, there was no way to have the gray areas that we've learned exists now, as adults. There were no gray areas there. It was all bright blue, you know what I mean? We did not have any comprehension of the real live factors that were basically working against us at that moment. If we had understood all of that the way that we do now, we couldn't have had such an intense and beautiful, exciting, and passionate exchange at that moment. Does that make any sense?
EVAN: Mm hmm
I love what he’s saying here, but also how he’s saying it.
He’s articulating the experience of having a clear perspective on a past version of yourself— with grace and generosity for us both.
At one point, we went outside so he could smoke a cigarette in his garden. LEO LOVER called his husband and we all chatted on speakerphone. I pointed my mic at the phone as his husband told me about his own exes.
Except for an abusive former boyfriend, LEO LOVER is in touch with all of his exes.
LEO LOVER: There's absolutely no point in me investing all my feelings and all my time into somebody that I'm going to be an enemy with later and not ever talk to ever again. No. I mean, what we had was super fun and beautiful and exciting and loving. And here we are 20 years later talking about it as friends and I think that's beautiful. Why not?
In my 20s, my tendency after a breakup was to self-protect and shut someone out of my life.
LEO LOVER was the first ex who reached out to me in the years afterwards to extend his friendship, which was an excellent model for me going forward.
Let’s take a Walk of Shame down Memory Lane…
With these 10 stories from the Hall of Fame.