So you want to date cis men, but it’s not as simple as it sounds. Perhaps you’re a trans woman newly navigating the change between dating men pre- and post-transition. Perhaps you’ve dated men for a while, whether you’re cis or trans, but struggle to do so safely and enjoyably. And perhaps you’ve never dated men at all, but now find yourself wanting to explore. I hope this guide will serve you—and perhaps even the men with whom we crave connection.
Let’s start with my credentials. I’m no expert in the art of dating men, nor would I trust anyone who claims to be, but I am a battle-hardened veteran of trying. As a polyamorous and at times promiscuous trans woman in my thirties, I’ve had countless experiences, from amazing to wretched, dating men who are cis, trans, straight, queer, bi, pansexual, DL (down-low), and/or confused. I first met someone off the Internet in 2011 and have since tried just about every dating app (though Feeld is the only one I still use). I’ve spent many years in the trenches with trans-attracted men, deciphering and responding to their strange behavior as compassionately as I can.
In other words: I’ve been through it, girl, and would love for you to learn from my mistakes.
This guide focuses on cisgender men, primarily those who date women. This is far from a homogeneous group, and I strive to avoid generalizations. I can’t speak to the intricacies of all cultures and backgrounds; your mileage may vary, and there are exceptions to every rule. That said: I’ve experienced certain patterns that are widely shared, and I believe that these patterns can be changed.
Though written from a trans perspective and with my trans sisters at the front of my mind, this guide is for everyone.
Figure out what you’re really looking for
This is a crucial first step; the answer may not be as simple as you think. I spent years “searching for a relationship,” only to look back and see that I wasn’t ready, or couldn’t accommodate one for various reasons (I was too busy, or frequently moving, etc.). It’s OK to want something casual—but being honest about that with yourself and others can prevent a lot of strife. Conversely, if you do want a relationship, communicate that early on, and be attuned to someone telling you (or giving off clear signs) that their end game is something different.
Take some time to really look inside; subconscious drives can be a bitch. In Aggregated Discontent: Confessions of the Last Normal Woman, a book that speaks to the experience of dating men as a trans woman, the writer Harron Walker describes “desperately want[ing] a boyfriend” while choosing “hookups masquerading as first dates.” She asks, “why was I so intent on trying to build a future with men who never seemed to want to build one with me?” The first step to solving this kind of conflicting behavior is to recognize it, then get real about what you actually want—and proceed accordingly.
Ask the right questions
Just as you need to know what you want, try to learn what the guy wants, too. Is he looking for a relationship, something casual, or a one night stand? Just a hookup, or something ongoing? If you don't want to be a guy's "first," ask early on about his experience with trans women. Your comfort and safety are important—ask whatever puts you at ease. It’s totally valid not to want certain things, and you don’t need to justify your reasons.
Sexual health practices matter, too. People can have different ideas of what constitutes “safer sex,” or “good sex” for that matter. I used to run down a checklist: When were you last tested? Do you use condoms? Eat ass? (This made me feel like I was conducting intake exams, but saved me from some poorly matched encounters.) Be prepared to answer similar questions, and take responsibility for your own sexual health as well.
Actions speak louder than words. Some people will tell you what you want to hear, or what they wish were true about themselves. Learn to be discerning, even when you want to believe. If you’re not looking for an immediate hookup, plan your first meeting in public—automatically weeding out anyone who has different intentions, or isn’t comfortable being seen with a trans woman—and don’t wait too long. This will save you from fantasy-fueled conversations that lead nowhere. People don’t owe you anything, but you also deserve to know where you stand.
Lower your expectations, but not your standards
This is a delicate balance. Expect too much—flawless communication; immediate prioritization—and you’ll burn out or shut down before anything can begin. Expect too little, and you may accept poor treatment.
For trans women, the bar is often on the floor. Raising my standards meant refusing guys who’d hide me, ghost me, or only hit me with a “WYD?” text after midnight. (It also meant focusing more on queer men than straight ones.) Lowering expectations, on the other hand, helped me stop overanalyzing every text or misstep, and give things space and time to grow.
Juno Dawson, who once wrote about being treated like a “24-hour sexual fantasy,” later found love with a cis man named Max, who she met on a dating app. In the 2022 book Conversations on Love, Dawson shares some of what she learned along the way: “You’re not meant to lose sleep or cry over love... If it feels like a fight, don’t waste your time.” For her, a guy being “too busy” to text back was an absolute dealbreaker. But if you’re just dating for fun—well, then draw the line at wherever things stop feeling fun! Everyone has the right to change their mind or pull back, but communication and honesty will always be key.
Consider… not dating cis men
Are you sure you want to date a cis man? Many of us fall into dating them because it feels like the default, or like a shortcut to affirming our womanhood. As trans YouTuber Natalie Wynn (aka ContraPoints) put it in her video “Shame,” in which she comes out as a lesbian after previously dating men: “There’s an intense erotic thrill in being desired… but excitement at the attention is not the same thing as attraction to men.” She is gesturing toward compulsory heterosexuality, or comphet, the idea that many people only believe themselves to be straight because it is socially enforced and rewarded.
Maybe you’re a lesbian—cue the legendary master-doc drafted by Tumblr user Angeli Luz in 2018. I’m sure not, though I have thoroughly explored the possibility. But there are other options! Personally, I learned that my core attraction was less to “men” than to masculinity, a quality I’ve found in spades among trans men, butches, studs, and non-binary people, many of whom can better understand my lived experience than cis men.
Of course, no one is suggesting you try to change your sexuality. And newsflash: people of all genders and sexualities can be toxic! However, it's worth looking inward and interrogating whether your desire to date men is stemming from comphet, and whether there are other avenues to explore.
Tune into the energy you want to receive
The people we attract are often mirrors—of what we want, or what we still need to heal. If you keep ending up with ashamed, repressed, or inconsistent men, ask what part of you is making space for that. You are never to blame for someone else’s bad behavior, but you might be subconsciously accepting it. As the journalist Diana Tourjee once wrote, “The obstacle between me and the affection I yearned for was a rejection of myself. In hiding their desires, the men who could not value me were rejecting parts of themselves, too.”
This isn’t about beating yourself up after a bad date, focusing on what you did “wrong.” It’s about asking: Do I believe I deserve the kind of love I claim to want?
Perry Gruber, founder of the Transamorous Network, writes extensively about using “the law of attraction” to find love as a trans or trans-attracted person. He uses examples from his own life and clients he’s counseled to demonstrate “how our stories shape reality”—a spiritual idea also found in evidence-based narrative therapy.
Continue checking in with your own motivations
Learning and healing is an ongoing process—continue peeling back the layers. Various motives might be steering our ship, and not all of them lead where we want to go.
In her new book Love in Exile, Shon Faye recounts the mindfuck of being pursued post-transition by the same type of “laddish” men who once bullied her. “Submitting to men’s desires sexually,” she writes, became “a way to gain power over them.” In response to being fetishized, she fetishized men back, becoming dismissive of their vulnerabilities. Explaining her mindset at the time, Faye writes, “Given that men could not be trusted, I did not have to respect their inner lives and was best off using sex to manipulate them.”
Faye recounts how she eventually realized that mutual objectification “warps and distorts you in the end.” On either side, fetishization closes the door to genuine intimacy.
Other dubious motivations might include dating to fill a void—Rupi Kaur once wrote that “loneliness is a sign you’re in desperate need of yourself”—or to meet societal pressures. If you’re really after connection and validation, consider self-partnering, platonic intimacy, and non-romantic relationships—all of which can also be explored on Feeld.
Have compassion—both for yourself, and for men
This doesn’t mean excusing bad behavior. But it does mean understanding that cis men are often lost. Punished for tenderness and fed lies about manhood, many are earnestly struggling. Psychologists have suggested that cis men depend on (and thus experience more turmoil around) romantic relationships more than cis women do, and according to the CDC, die by suicide four times as often.
As bell hooks wrote in The Will To Change, “The first act of violence that patriarchy demands of males is… psychic self-mutilation, that they kill off the emotional parts of themselves.” Men can have different experiences—there are billions of them, after all—but it’s useful to consider how gendered expectations influence everyone’s approaches to love and relationships, especially for the specific men you’re dating.
Remembering that we are all working through shit creates space for both you and your lovers to grow. Tourjee, who spent years documenting the stories of trans-attracted men—even when those stories were grim— experienced this first hand. “As I have aged in transition,” she wrote, “I have come to know countless men who are open about their attraction to women like me. Sharing my bed with those men allowed us both to experience true intimacy.”
Enjoy yourself
Dating men doesn’t have to be a constant trauma workshop. Yes, cis men can be clueless, messy, repressed, and self-centered—but so can anyone. And they can also be intelligent, sweet, funny, and emotionally present. Not every flirtation needs to become a life lesson. Sometimes a date is just a date, a kiss just a kiss. Sometimes it's nice to let yourself be held.
You don’t need to define every situation right away: I’ve had sweet, fleeting romances with men I barely remember, and lifelong friendships with men I used to sleep with. And I’m just one person! You might read more, or simply ask, about how other trans people feel on these matters.
Ultimately, the best way to learn will be by putting yourself out there, if and when you feel comfortable. When you’re ready to explore, and perhaps be pleasantly surprised, we’re waiting for you on Feeld.
