HEART TO HEART
Looking for Love and Acceptance: Dating While Trans in America
The Daily Beast spoke to transgender people across the country to find out what challenges they face in relationships.
In the third season of Transparent, Maura Pfefferman goes where the character has never gone before: the bedroom. After Pfefferman, played by Emmy-winner Jeffrey Tambor, meets Vickie (Angelica Huston), a breast cancer survivor, at a women’s music festival, the two quickly strike up a romance. It’s a first for the groundbreaking Amazon show, which has depicted the pressures of coming out and dealing with acceptance frankly but has yet to explore the topic of dating while trans. Elsewhere, Maura’s son, Josh (Jay Duplass), develops an attraction to Shea (Trace Lysette), a stripper who challenges his ideas of who transgenderwomen are.
Telling these stories is extremely important. A survey from Match.com published in May showed that trans people, even as they have made strides in media representation, continue to be discriminated against by potential partners—even by others in the LGBT community. Just half of LGBT singles said they would date someone who is trans. (Match.com is owned by The Daily Beast's parent company, IAC.)
Over the past few months, The Daily Beast has spoken to transgender people across the country about their romantic lives and experiences—whether it’s being turned down by partners or finding acceptance. Their answers are varied and wide-ranging, but they show a great deal in common: Dating cisgender men is a challenge, but cisgender women and other trans people are easier. The interviewees the Beast spoke with are searching for love but also validation—to feel wanted and desired.
To read their responses, collected through phone interviews, is a reminder of the universal struggles and need for connection that make us human.
Jen Richards, Los Angeles, Calif.Actress and activistTrans woman, she/her
How dating as a trans person has changed since she first came out:
“So much has changed in just the last five years. When I was beginning to transition, the consensus online was that transition was a means of last resort because it inevitably entails losing your job, losing your family, losing your relationship, and having to start life over completely on your own and never dating again. The kind of dating communities I was a part of were just full of tragedies, where that was considered the norm. I didn’t know any trans women who were in long-term relationships. I saw no model for that. There were no trans people in the media. We weren’t even very visible on social media yet. It never occurred to me that it was possible that someone would want to date a trans woman.”
On disclosing her gender identity to partners:
“I always start from the assumption that the possibility of a relationship is over the moment I mention I’m trans. I would often find myself delaying disclosure because there’s this the moment—this little bubble, I called it—where I was just a girl, talking to a boy and there were possibilities in front of me. I knew the moment I told him I was trans, that bubble was going to burst. There was always a chance that they would say, ‘Oh, that’s great,’ but incredibly unlikely. So I like to live in that moment.
“There was this one situation where I met a guy on an airplane. I travel a lot. We had talked for a week. I really liked him a lot. After we started emailing one day, he looked up my email address and found links to me. He emailed me an hour before our date and said, ‘I just found out what you are. I have no interest in that. Goodbye.’”
What it’s like to date women as a transgender woman:
“Women haven’t had an issue. I’ve been asked out by lesbians, not just bisexual women. I’ve been with lesbians who have never dated a man and who have never touched a penis. But so far in my experience, they’ve all been unfazed.
“The first time that a clearly lesbian-identified woman pursued me, it meant the world to me. It was one of the most affirming moments of my womanhood—being desired and pursued by a lesbian-identified woman. A lesbian who is a woman who loves other women, and there being a long tradition within lesbian community of exclusion of trans women…to have women who love women pursue me, it just means that much more.”
Devon Shanley, New York, N.Y.Public school teacher, 34Trans man, he/him
On dating for the first time after he moved to New York:
“Because I felt so isolated, I found myself feeling more vulnerable and a little bit scared. I didn’t date that much. I had ended this four-year relationship. I was by myself. I had some really good friends I went to college with who were New Yorkers, so I had a really strong support group. But I didn’t end up dating that much. I went almost entirely on a three-year span of not dating. That’s because the times I did almost date, I was turned down.
“There was an friendship I’d developed over a long period time with the brother of a close friend, but he had not known that I was trans. It led to a situation where we were literally making out in the rain and coming to my apartment, and I had to do that last-minute disclosure thing. He was a gold star gay boy and got nervous and ran away.
“The people who I became interested in afterward, I didn’t really expect to be treated fairly. I became self-protective and just closed myself off.”
When he came out to his current boyfriend:
“My current partner is six years younger than me and really good looking. He went on a date and we were at Mercury Lounge, and my friend was performing. I felt like I didn’t want to create the space to feel vulnerable again; it wasn’t a safety concern or a fear there was something wrong me. I didn’t want someone else’s issues to make me feel uncomfortable. He didn’t know any other trans people and had never been with any other trans people. I didn’t want to be someone’s teacher: ‘This is what’s right, this is what’s wrong, you shouldn’t say this.’
“Now he’s become part of the community. He’s in conversation with trans women and men who are friends of mine. He does little things every human should do when they hear somebody say something negative or use derogatory terms about trans people—he will school people on that. He’s not looking for a sticker, but he’s proud of himself for knowing that we’re all in a different space.
“All of this is to say that, surprisingly, things worked out. We live together, we’ve been together four years, and we’re in a monogamous relationship.”
Karari Olvera, Chicago, Ill.Organizer for United Latino Pride, 31Genderqueer, they/them
On being told to look more masculine:
“My last ex, one of the fights we had at the very end, he told me that my hair was ‘disgusting’ because it was longer than his mother’s. That really stung.
“Hair, for better or worse, tends to absorb a lot of things. If I’m outside, my hair will often smell like wherever I was. If I’m at a barbeque, my hair will smell like smoke. But I also feel like my hair absorbs a lot of things, energy-wise. If I absorb something, I carry it with me and it feels almost like some kind of strength.
“As it grows longer, I feel much more defiant of conventional gender norms. For me, it’s my way of staking a claim in this world. It makes my gender non-conformity and my gender very visible. That’s something that’s very important to me—to be seen as genderqueer. It makes me empowered to know that people can tell and that they can somehow sense my variance. To have someone tell me to cut it is to tell me to cut part of myself off. I take it very personally.”
How coming out led to the end of their relationship:
“My last relationship ended because not only did I change genders, I also changed my name. It was very hard for him, having met me as my legal name, to adjust. He had fallen in love with the first person he met. He wasn’t falling in love with the person that I was continuously becoming every day. For him to be forced to let go of that memory of me, the first person he met, it was difficult for him. He fell in love with me one time, and he expected me to stay the same.
“Calling me by my name was a struggle. He would still call me by my birth name. He tried, but he eventually stopped calling me by name at all. He would grab me or touch me instead. It made me feel invisible.”
What it’s like to date other genderqueer people:
“Oftentimes, I’m attracted to a little bit more femininity. I’m not particularly attracted to hypermasculine men. They often exhaust me. There are so many rules associated with their masculinity and it’s so fragile that these minor things will completely scare them away.
“I really would rather date other genderqueer or gender nonconforming people. The problem is there’s this very limited notion of who we’re supposed to date. A lot of it is that we don’t celebrate trans love—or love between trans people. We focus on the men who date trans women, the women who date trans men, or the cis people who date trans people. We hold them to a very high regard, ‘Oh, these people love us—even though we are trans,’ when we really should be saying that trans people loving other trans people is radical in itself. We’re hardly supposed to love ourselves, let alone each other.”
Jessika Gonzalez, Phoenix, Ariz.Nurse practitioner, 28Trans woman, she/her
On being told that she’s not “girlfriend material”:
“Dating anywhere in any town and any state that I’ve lived in has always been the same. The guys that I meet are straight, cisgender guys that are more looking for the taboo factor. My friend, Miguel, he told me, ‘Jessika, men are always going to see you as a passport, just because you’re so feminine, they’ll be to tell themselves that you sound enough like a woman, you look enough like a woman, and you act enough like a woman that they’ll be able to tell themselves you’re passable enough.’
“It’s very rare that I find a guy who is willing to go on a date. The ones I have gone on actual dates with—to the movies, dinner, or to play putt-putt golf—in the end, they always ask, ‘Well, can we go back to your apartment and have fun?’ And that’s the end of it. There’s no second date. I’ve asked them, ‘Is it me? Is it because I’m transgender?’ They said, ‘If I wanted to find someone to settle down with or a long-term girlfriend, I want to have someone I can bring home to mom, that I can have a life with, and that I can have a family with. I can’t have any of that with you. I can never introduce you to my family or my friends.’ It’s hard.”
Why she chooses to not disclose her gender identity to partners’ family members:
“If there is going to be any family get-together on his side of the family, family barbeques, quinceañeras, birthdays, or anniversaries, there’s always going to be family members who haven’t been told yet or don’t realize yet. That will be the topic of conversation. I would be the focus of it. As long as they believe I’m a straight cisgender woman, it makes everything easier. There’s no gossiping. There’s no whispering. There’s no side glances. There’s no one getting drunk and opening their mouth.
“Like an actor or actress, if you can get your audience to believe that character is really truly you—not just Angelina Jolie playing Lara Croft. If you can get your audience to believe that Angelina Jolie is actually Lara Croft, that’s the sign of a great actress. So for me, if I can get my get audience to believe that I am a full cisgender woman, I’ve done my job.”
Melvin Whitehead, Chicago, Ill.Librarian, 33Transgender man, he/him
When he began to date men after his transition:
“I was planning on just dating women before my transition. That began to change once I started testosterone. The person I first started dating three months into my physical transition was a woman. And then over the course of that relationship, I realized I was more attracted to men and less attracted to women.
“It was very confusing for me because I had been attracted to women all of my adult life and through my teen years. I came out in high school—I was 15. I didn’t want to be a stereotype because there’s a stereotype in the community that [taking testosterone] makes you gay, which is totally not true. It’s a huge thing within the trans male community—because so many trans guys develop an attraction to men or become more comfortable acknowledging attraction to men. It’s totally a thing, and I didn’t want to be that thing.
“I struggled for a long time with it. I kept dating women. After [my girlfriend and I] broke up, I moved to Illinois and went on these dates with women that were totally my type prior to transition. There was this one woman I had been dating for a month. I hadn’t even kissed her, and I didn’t want to kiss her. Things were moving really slow with us and we eventually stopped seeing each other. I realized that I just wanted to be friends with these women.
“Once I actually admitted that to myself, it was like, ‘Oh, I am still gay. Just not the same way I was before.’”
What the difference is between dating men and women:
“Dating women was a lot easier. In my experience, women were a lot more flexible in their sexuality. I dated straight women. I dated queer women. They didn’t have any issues with my transition. When it came to dating men, it was the opposite of easy. I found a lot more men had a lot more hang-ups around dating trans men than the cisgender women I had been seeing before.
“A lot of it was ignorance. A lot of them had never met a trans men before. Many of them assumed what my anatomy was—that was really common. They would say, “I don’t like vaginas” or ‘That’s gross.’ If I put I was trans in a profile on a dating website, they would think I like to wear dresses. People were really confused as to what trans was.”
On getting rejected by men:
“A couple years ago I was in D.C., which is where I’m from, visiting my mom for the summer. I went on OkCupid. [Ed. note: OKCupid is owned by The Daily Beast's parent company, IAC.] I wanted to see who was around. This one guy hit me up. He was totally gorgeous. We went out to lunch on his lunch break. We had such great chemistry that he ended up staying two hours on the date and he wanted to stay longer. After the date, he texted me. He said he thought I was really cute. He said it was refreshing to go on a date someone like me. He asked if I would like to see him the next day.
“Normally, I don’t go on second dates the day after the first date. It seems like a little much. But I thought he seemed really cool and I wanted to hang out with him again. The next day we go out and we go out to this Thai restaurant. Afterward, I decided to take him out for a smoothie for dessert. We go to this place across the street. I’m paying for the smoothies and he sort of playfully grabs my license and he looks at it. In the license photo, I’m smiling a huge smile because it was the day I got my legal name change. It was a big, cheesy smile. He was like, ‘Why are you smiling so hard?” At this point, I hadn’t told him. I thought about not telling him, but I thought, ‘This is the moment.’
“After I told him, the whole mood changed. He became less talkative. I paid for the smoothie, and we started walking to his car. I asked, “What’s wrong? Is it the trans thing?” He said, “Yeah, I don’t know if I can date you.” He texted me at around 2 a.m. the following night and said he just wanted to be friends.
“Sometimes I have those moments, it’s really rare, where I hate being trans. I felt really shitty about it. But I try not to stay in those places when I get like that.”
Michael Miller-Ernest, New York, N.Y.Student, 21Transgender man, he/him
Why he’s concerned about safety while dating online:
“Most of the time I dated was through Tinder and other online dating sites. I’m not expressly out on those sites. My name says ‘Michael’ and they see my picture. I get kind of ashamed, but I’m really scared to go out with strangers and put that out there: ‘Yes, I am transgender.’ You don’t know how people will react.
“The person I’m talking to is somebody who I’ve never met before and if I don’t know what their intentions, there’s always this concern that I’ll put out there that I’m trans, we’ll talk, and they’ll set up a time and a place for us to meet out in public somewhere. What if I show up and they’re not who they said they were? What if their intention is to hurt me? It’s self-preservation.
“As much as I want to put myself out there, meet a great guy, and get into another relationship, I also need to protect myself.”
What it’s like to get asked uncomfortable questions on a date:
“It does get kind of awkward. People don’t know what to say or it turns into this Q&A about my identity that I don’t want to have—because people ask invasive questions and I’m like, ‘I just met you! I don’t want to tell you about my genitals. At least wait until the second or third date.’
“When you enter into a romantic scenario, people think it’s cool to ask anything. A lot of people, I’m the first trans person they meet or one of the few they know. ... If it’s my friends, I know it’s my friends and they’re not being assholes about it. But with strangers or people I’ve just met, I’m like, ‘You can find that information online. Somebody’s answered that already.’”
On having his body policed by partners:
“If I’ve had sex with somebody and I’ve already been intimate with them in that way, I get asked, ‘Why haven’t you done this yet? Why haven’t you done that yet?’ The image in the media and in news stories is about young transgender people, kids who were my age when they came out, 14-year-old and 15-year-olds who have already started on that transitioning process. I have to explain why I didn’t start doing hormones in high school. I haven’t even legally changed by name yet. It’s expensive and it takes time, and I don’t have time for that right now.
“There’s an expectation of a timeline: ‘You’ve been out for seven years. Why haven’t you done more? Are you actually trans—because you don’t wear a binder, you haven’t had surgery, and you haven’t written a biography about yourself?’ I don’t have a reality show, and I haven’t been on Ellen yet, so I must not be actually trans.”
Kimberly Horne, New York, N.Y.Software developer, 38Transgender woman, she/her
Why dating cisgender men is a challenge:
“They’re worried that being interested in you makes them gay. This is a huge fear for them—at least for straight men. They generally don’t want to be seen with you. If you’re a straight cis guy, it means weathering a bunch of teasing from your friends, it means educating them, and it means educating your family. There’s a lot of work involved, and I think that a lot of people just don’t want to do it.”
On trying to find a partner online as a trans person:
“If you’re on OkCupid—as a trans woman or otherwise—it’s like turning on a fire hose of assholes.
“The worst is this guy who kind of looks like a bodybuilder. He’s just obsessed with boobs. Every couple days, he sends me a new message about how he wants to motorboat me—no context, no anything else, just ‘I want to motorboat you.’ It became a running joke in my life: Is the motorboat guy going to message me today?
“If I go one OkCupid and don’t tell people I’m trans, I get one kind of jerk. If I do tell people I’m trans, I get a different type of jerk. There’s pain no matter what side of the fence you’re on. If I don’t tell people I’m trans, I get a lot more of what look like real messages—people who are trying to charm me in some way. It may not go anywhere, but they put in some effort. If you advertise that you’re trans, they put in no effort whatsoever. It’s just garbage—because they know they can get away with it. They think we’re desperate for attention: ‘This is the only message she’s going to get today.’”
Why it’s not getting better:
“The problem with me is that I’m 38, and I’m trying date people who are around my age. After awhile, people don’t really change. They’re stuck in their ways. Imagine you’re a trans kid who is 18, 19, or 20. Your dating options when you’re 38 are going to be very different because they’re people you grew up with—who grew up with the notion that trans people exist and it’s OK. I think that people my age are a ‘lost generation.’ It’s probably not going to get better for us, while it gets a lot better for the youth.”
Jacob Tobia, New York, N.Y.Writer and advocate, 24Gender non-conforming, they/them
How coming out as gender nonconforming has affected their sex life:
“It’s been pretty bleak, to be honest. I rarely date. Hooking up is really hard. It creates a negative feedback loop. You get negative reinforcement from other people, like when you’re at gay bars. That hurts your confidence which leads to more negative reinforcement. It’s a cycle that a lot of us are trapped in. It’s tough.
“I certainly know for a fact that when I presented as masculine, I got a lot more action and a lot more interest. The second you let your wrist fall limp, you wear a pair of heels, or you grow your hair out a little bit, it’s game over for so many folks in the gay community.”
Why it can be difficult to date as a trans person:
“My roommate is a trans woman and we commiserate all the time that it is so hard to find people who will date us, admit to our attraction to us, and be happy to embrace that publicly, because our identities are so stigmatized. Admitting that you’re attracted to somebody or love someone with a stigmatized identity is just about as bad or takes just about as much courage as having that stigmatized identity in the first place. Admitting that you’re dating a genderqueer person and taking someone like me in a little Jackie Kennedy dress or to some work function with all your cisgender heterosexual colleagues, that’s going to be just about as hard as if you were the one in the dress.
“It’s not like people don’t see us as sexy now. It’s just that everyone’s ashamed to say it. But there are so many people who walk down the street who think I’m gorgeous—because, like, I am cute. But no one knows how to admit that. Everyone has all this shame about finding me beautiful in my heels with my leg hair. There’s nothing shameful about finding me beautiful, but people have so much internal work to do before they can admit that.”
Erica Johnson, Chicago, Ill.Senior software developer, 43Transgender woman, she/her
On coming out while she was married:
“When I first came out, I was married. The four and a half months she lived with me after I transitioned were the most hellish months of my life at that point.
“It was difficult. She did not like that I transitioned. She had been aware of my gender identity from when we started dating, 10 years prior to that. We talked about it throughout the entire course of our relationship. She didn’t like it at all. She didn’t want to be married to a woman. It became a serious problem. We would have arguments about it. Any time I showed signs of femininity, if I dressed up around the house or dressed up to go and meet friends, she refused to join me. She didn’t want to be seen with me. It was smothering.”
What it was like to date trans women for the first time after the divorce:
“I met some other trans people from the local community. I thought, ‘Am I up to dating a trans woman like myself? Do I consider this person to be a woman the same way I consider myself to be a woman?’ I had to constantly think my way through it. I had no experience dating queer or trans people before that.
“That was weird for me to get around at first, but then I was like, ‘She’s a woman just like me.’”
On her current partner, who is transgender:
“It’s been really great. We can talk about what we’re dealing with very openly. We don’t have to be closed off.
“We call each other every night. We text every day, say I love you. But when we are together, it’s like the best thing in the world. It’s so infrequent. She lives in California, so we see each other once every four to six weeks on average. In mid-July, we are going on a vacation. She’s bringing her kids. We are going to a lake house in Virginia. Her whole family is going to be there. It’s going to be great. It’s really wonderful to have these times just being together with each other and everybody respects everybody.”