Today we debrief with Lee Shmueli in Newton Centre, who responded to my request for breakup stories. We also build on last week’s call to listen to stories about gender and transition.

created at: 2013-11-18I met my first boyfriend when I was 14. We broke up when I was 20. We were practically married and, to this day, sometimes lovingly refer to each other as “hubs” or “wife.”

Soon after we broke up, I departed for the epic adventure that was study abroad in Finland, just south of the Arctic Circle. I met a man; we’ll call him Seth. He was gay. I was female-bodied. I fell in love with him and subsequently came out as a lesbian. I am aware, now, that the lesbian thing might have made more sense were he a woman. For me, I identified with him being a gay male, so I also identified as gay. I was a masculine, female-bodied person who fully enjoyed men in all their fabulous glory. So I identified as a lesbian, thinking that would address my confusion.

Seth and I would cuddle, go to gay clubs, dance and share intimate emotional moments. After study abroad, we returned to campus, signed up for the same class or two, and moved in together. We were inseparable—except during his sexual encounters with the men he was dating. We continued to enjoy both physical and emotional closeness, which felt…ambiguously platonic. One day, I looked at him and said honestly: “I am in love with you.” I never really got a response, and we continued with our ambiguously platonic closeness. Looking back, I am certain he was ambivalent. He must have felt something for me, at least.

A year into our friendship, I looked at Seth and his partner, and vocalized what I’d been feeling: “I am a gay man in a woman’s body.” A love triangle of support ensued, although I first attempted to be a straight girl dating men.

When looking at an online profile, or when flirting with the random guys I met in coffee shops or bookstores, I would catch myself asking, “Is this guy gay?” Time and time again I would put myself down, thinking: “Stupid girl! Not again! You are a woman! What does it matter if he is gay?”

When I moved to Israel, things went downhill with Seth. The distance posed a challenge to our already complicated relationship. For the next two years, we cycled through taking breaks, trying to reconcile, and returning to disappointment. We had misaligned desires, and I was not being honest with myself.

Last January, after almost seven years, Seth and I parted ways. I was free from what had actually been a tumultuous and dysfunctional relationship. For seven years, I thought my relationship with Seth and my love for him was driving my masculinity and fulfilling my desire to be more than “a gay man in a woman’s body.” But I know that was an excuse not to move forward, not to seek resources around transition, and not to love myself more than I loved him. He was my masculine and male-identified role model—he was who I wanted to be.

created at: 2013-06-17I approached it just like a breakup, even though there wasn’t an explicit romantic relationship between us. Within minutes, I was on the phone crying. I felt like a piece of me had gone missing. Over the weeks that followed, I returned his things to his front porch and wrote letter after letter that I never sent to him. Friends listened; I cried. It was a breakup because it was so broken.

I moved forward and took every step of transition. Things are looking up for me! Step by step, I am beginning to present myself to the world as I see myself. My masculinity does not depend on the body and identity of another person. I do not have to live vicariously through another man. If I ever had a doubt about my identity, it was quickly shot down by the joy of my first time being read as male in a gay club. I am actually happier than I have ever been.

Lee invites you to email him with questions or reflections at LeeShmueli@yahoo.com. And, as always, contact me at mimia@jewishboston.com to share your own stories about love, heartbreak, gender, identity, or anything your heart desires.

*Photo by Lee Shmueli

The Debrief appears every Wednesday on JewishBoston.com. Read past columns, or contact Mimi at mimia@jewishboston.com.

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