When I started this experiment, I didn’t particularly believe my exes had anything to teach me. I figured that when I contacted six people I dated to find out where I and/or our relationship went wrong, I would get to watch them squirm. I pictured their responses in my head — they’d say I was too weird, too emotional, too much — and I would clap back with pre-planned rebuttals.
Instead, I found myself surprised by their answers, and talking to them showed me so many things about this person I have become. Maybe I’m just lucky to have dated incredibly wise and introspective people, but I almost wish I’d done it sooner. I challenge you to do it, too.
The Middle-School BF: Gary
Gary and I dated for nine months in the seventh grade until he broke up with me out of the blue and started dating someone else. It was true middle-school heartbreak. He lives across the country now, so I had to call him via Facebook Messenger. He immediately groaned upon picking up.
“Ugh, I’m just so stoned right now,” he complained. “And that’s so much to unpack and analyze. But fine.”
“Okay, full honesty, where did I go wrong?”
He laughed and said, “You were a woman.” He paused a little before elaborating. “I was incredibly far in the closet and also so sexually naive that I didn’t understand what my attractions were or meant. Also, you were a little much.”
Gary’s mannerisms had also always signaled queerness to our peers; I remember everyone was surprised to learn that we were dating. And watching the way they spoke about him as “gay,” when he wasn’t even labeling himself as such, contributed to how ashamed I was to like other girls. I was desperate for everyone to believe in our relationship, because I thought it would protect me from being identifeid as bi or queer by others.
The Plagiarist: Joseph
During my freshman year of high school, someone handed me Joseph’s composition notebook. The first page was a letter that included the words, “I can see us holding hands, walking on the beach, our toes in the sand. I can see us in the countryside, sitting in the grass, laying side by side.” If that sounds familiar to you, it’s because those are Justin Timberlake lyrics. I agreed to be his girlfriend anyway.
We’ve been texting lately, so he was the first person I contacted for this — I knew it’d be an easy Band-Aid to rip off.
“I liked that we were legit just friends who kissed on more occasions than not,” he told me. “I just didn’t like feeling like I was pressuring you for things you weren’t interested in at that time, aka sex. And I didn’t like feeling like I couldn’t make you happy.”
I’d always thought my sexual inexperience had been covert. I was raised in a very religious household where I’d had sexual purity and standards of “respectability” drilled into me. I suspect I imagined that relationships were supposed to be essentially platonic until you got married (which is probably why I didn’t question the fact that Gary and I never kissed or held hands).
So dating Joseph was a tad overwhelming. I couldn’t even hear a sexual innuendo from him without bugging out, and sometimes very benign things he did, like putting his hand on my waist, translated to objectification in my head. I wish we’d had a better template for dating and sexual development back then, maybe one that wasn’t completely entrenched in shame.
The First Love: Jomo
I dated Jomo for almost two years in high school and early college. I’d promised my family and church that I would wait for marriage to have sex, so I was convinced that losing my virginity would prove I was a bad person unworthy of respect. When Jomo and I finally had sex, I had so much shame in my body, but I couldn’t talk to anyone about it.
Then I got to college, and that feeling started to lift. I was finally exposed to women who were having shame-free sex — and not just in committed heterosexual relationships either. I made friends who were openly gay, which validated aspects of my own bisexual identity, and I became less attached to respectability politics overall. But every time I tried to go out with my new friends, it turned into an argument with Jomo. It felt like he didn’t trust me.
“I felt like you couldn’t be your 100% authentic self and be with me at the same time,” Jomo told me. I was shook. This was more accurate than I’d expected. “I feel like we were both at a point where we were discovering who we were and who we were willing to be. When you were around your friends or otherwise not around me, you’d be an entirely different person. When you’d say you were happy, I’d doubt that knowing that there were parts of yourself that you weren’t comfortable showing me.”
I never understood why Jomo broke up with me and thought it reflected his lack of trust, so it was interesting to learn that there was something deeper behind it. And even though I didn’t appreciate the breakup at the time, it totally needed to happen.
The Ex Who Might Hate Me: Roberto
I met Roberto at a major turning point in my life. I was just becoming this loud, passionate feminist, but we’d argue about me wearing revealing clothes or posting certain pictures. I had finally accepted that I was bisexual, but I couldn’t fully explore my attractions to women while in that relationship, so I advocated for us to have a threesome. Roberto exited the relationship shortly after that suggestion. I spent years wondering whether if I’d only been a “good” woman, if I’d just ignored my own queerness, I’d still have him. I was pretty sure he hated me and wouldn’t agree to participate in this experiment, but I sent him a DM anyway.
He responded three days later, saying, “I take the full blame for the way things ended. You were awesome. I thought I knew more than I did. About all things. Which is pretty ironic, seeing as how it was when I met you that I learned so much more. You showed me perspectives I never even considered and taught me lessons that broadened my outlook on almost everything.”
I let go of some shame I didn’t even know I was carrying when I read that.
The Reason I Came Out To My Mother: Ashanti
Ashanti was the first woman I fell in love with. I tried not to. I intentionally pushed her away at first. I was so scared of my family finding out. Even though I intellectually knew that liking women wasn’t wrong, I felt as if I was doing something naughty. But I genuinely connected with Ashanti to the degree that I started seeing a therapist to work through those feelings. Looking back, I wondered if I was so intense that I pushed her away.
I called her to get to the bottom of things. She insisted on hanging up and texting me her answers.
“There was nothing you could’ve done or changed to make us work,” she wrote. “I had so much fun with you and that may sound so simple, but when I met you, I felt as if I was talking to my best friend. I loved that about us. It wasn’t us as a couple [that was the problem], it was just the way I look at things.”
Despite our connection, she told me she was uncomfortable with how different we were. So I guess no matter what, I could never overcome her perceptions.
Reconnecting with Ashanti showed me that I don’t have to be ashamed of that experience. She’s a huge part of the reason I came out to my mother. I loved Ashanti so much that I wanted my mom to know who she was to me. I don’t think I would’ve had the audacity otherwise.
The Tinder Match: Lin
Lin, who I met on Tinder, is such a special human being. We were dating casually but she never really seemed to reciprocate my feelings. And then, Ashanti called me to tell me she got married, and I felt like I was being rejected by two people simultaneously. I took a break from dating at that point.
“The reason we didn’t work out was because we both were not willing to separate from our careers and our lives,” she told me. “We are both workaholics, which didn’t leave time for things outside of work. Perhaps we need partners who aren’t as invested with work to show us another side of life. Perhaps we were just too stubborn to really want to allow for sacrifice.”
Ater navigating shame my entire life, writing about sex and identity has been a healing experience for me. And Lin’s right, that’s not something I am presently willing to sacrifice. I don’t think I really recognized that until I did this experiment.
When I look at these relationships in order, I can track my self-love journey through the reasons each hasn’t worked out. So apparently, there’s value in closure after all.