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Voices of Transition: Trans Dating Tips From Trans People

Madison Werner and Seven Graham have different stories to tell about trans dating. Here are their tips.
Madison Werner
Seven Graham
Guest Writer
February 22, 2024
April 16, 2024
min. read
Table of Contents

Assumptions get us into trouble, especially regarding love and desire. Our preconceived notions about gender and sexuality can lead to misunderstandings and hurt, even with the best intentions. Two voices are here to help us see things differently.

First, there's Madison Werner, a trans woman and advocate who understands the unique landscape trans women face when dating—both on and off the apps. Madison's advice includes the subtle ways internalized homophobia and transphobia can rear their ugly heads and sheds light on how to better create spaces for understanding.

Then, there's Seven Graham: transmasculine, a therapist, and a comedian who helps challenge the stereotypes some might have about sex & dating on apps like Grindr. For him, it's about unlocking desire and embracing the hard-won authenticity that came with overcoming addiction and discovering his intersex identity. 

Together, Madison and Seven offer tips based on first-hand experience that provide a kind of roadmap for others who might be navigating the complicated world of dating as a trans person. Read on for their unfiltered takes on love, desire, and all the messy, beautiful things that can come with trans dating.

Madison's Insights

Sexual Orientation and Responsibility

Not entirely sure about your sexual orientation or how you identify? Don’t make that her responsibility. Due to societal pressures and expectations, when cisgender straight men are attracted to trans women, they often worry whether they’re gay or if their guy friends will emasculate them. The pressure to conform can lead him to keep his trans girlfriend a secret, avoid commitment, and unfairly blame her for his own insecurities. It’s where homophobia and transphobia intersect: fear of being gay and fear of attraction toward trans people. Trans women experience enough difficulty every day; having confidence in your sexuality takes the pressure off of her journey toward love.

Physical Safety

Be mindful of her physical safety in the spaces you bring her into. Your friends, family, or coworkers may be gay-friendly, but being trans-friendly requires a different level of understanding. Trans women are often hyper-aware of new surroundings due to safety concerns. If you want to be her partner, developing this awareness is helpful, too. Have the necessary, private conversations with people in your life before she meets them.

Respect and Understanding

While it’s important you’re aware of her trans identity, don’t immediately ask questions about her gender transition. Talk to her like any other girl you’re attracted to: one step at a time and with respect. Gender transitions are as personal as it gets, so let a trans girl tell you about it when she’s ready to or when your relationship emotionally deepens. There are many things to know about her personality, not just her transness. If you're seeking knowledge about gender transitions in general, a quick Google search will do the trick.

Communication in Intimacy

Some transfeminine people experience gender dysphoria (a mismatch between their gender identity and their body), which can impact their sexual experiences. Let your trans partner communicate about it if she feels the need to. Just like cis people have turn-ons and turn-offs during sex, trans people may have them about their trans bodies. Hold space for it.

Celebrating Transness

Make it clear, via affirmations and actions, that her transness is not a burden; it’s worth celebrating and just makes her even more beautiful. Her identity is a reflection of her authenticity and closeness with herself—qualities that should be cherished in any person regardless of gender identity.

Seven’s Insights

Communication is Key

Since starting my transmasculine journey with testosterone shots in 2018, my libido has been freed from the fear and shame that used to hold it back. Now, Grindr is my go-to app when I'm feeling horny and looking for some fun with like-minded people (although I’m still looking for a “Classy Orgy”). Discuss feelings, concerns, and expectations openly. Good communication helps build a safe, strong foundation. I say it like it is: Deal or no Deal!

Educate Yourself

It’s not trans and intersex peoples’ job to educate you. Learn about trans and intersex issues, terminology, and experiences to understand your potential partner's perspective better. Accept that some trans people don’t want to play with cis people, even if you are gorgeous and God’s Gift—T4T means trans for trans. Furthermore, trans people come in many genders. “Trans” just means a person whose gender does not correspond with the sex registered at birth. 

Respect and Learn About Trans Peoples’ Experiences

To overcome my addictions in rehab in 2001, I learned that I had to get really honest about who I am to overcome the huge shame that drove my alcohol and drug use. In my teens and 20s, I couldn’t flirt or have sex without being super high.

Most LGBTQIA+ folks have some degree of shame from growing up “different,” but I was born intersex: biologically a mix of both the two common sexes. I’d been AFAB (assigned female at birth) because I had a vagina (I still do—I call it manpussy, or front hole, now), but I never felt female. Unbeknownst to me or my parents, I have XY chromosomes and was born with internal testes (stolen from me by doctors to fit me in the female binary box).

My experience makes me uniquely me, giving me a lifetime of stories that at least make for good stand-up material. But along the way, I've realized that my struggles are just one tiny piece of a much bigger picture. That's why it's important to listen to and respect the experiences of the trans community.


Just because you are comfortable sending intimate photos doesn’t mean everyone else is. For example, as an intersex person, I never send my genitals in a picture because they would be sold to a porn site. 

In 2018, I decided to ditch the estrogen my doctors put me on at age 12 and try testosterone shots (t-shots). I soon grew facial hair, and my “large clitoris” became a dick. It’s still growing “like Jack’s fucking beanstalk.” So now I have something for everyone. But to see them is real-world only. We intersex didn’t have a choice over who saw us as kids, and it’s an important boundary to respect—my genitals are my genitals, not for those on the grid. And that’s my choice. Your dick may be a handsome specimen, but that doesn’t make it front-page news—or appropriate to send without consent.

Be Patient

Understand that the process of self-discovery, acceptance and trust can take time. If you are FWB or getting into a relationship with a trans partner, be patient and supportive throughout their journey. Meet them where they are at, and if you’re lucky, they’ll meet you right where you’re at, too.

About the Authors

Madison hails from Calabasas, CA and came out as transgender in November 2015. She's now a trans rights advocate, writer and self-proclaimed "trans glam girl." She uses her social media to cultivate a safe place for queers and allies to learn about the trans experience. You can follow her on Instagram here.

Seven Graham is an LA-based UK-qualified addictions therapist & creativity coach who helps Hollywood tell intersex and trans stories. You can find everything you want to know about Seven here.

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