Sexpert: Trans* dating tips

Dear Shanna,

I’m older and grew up surrounded by 1950s sensibilities. I’m a cisgender heterosexual male. I have been seeing a trans woman. I’m attracted to her, but … nervous, perhaps … unsure and not quite able to express my uncertainties about stepping further into physical intimacy with her. I sense that it’s MY stuff that’s in the way. Any ideas?

— Needing to Unpack Some Baggage.

Simply by calling out the fact that you have some stuff to work through, you have already taken a step forward on figuring out a solution to your challenge. Way to recognize that each and every individual comes to a relationship with their own “stuff,” and that it is not up to the other person (or persons!) in that relationship to educate them and help them through that process, unless they so choose.

Stop for a moment and think about what your fears are; are they just that this is a whole new situation, and you don’t want to do anything “wrong?” If so, maybe chatting with her about your concerns, and your intentions, and coming up with a “What If” plan is exactly what you two need in order to move forward.

Is it something deeper and more socialized around fear of “otherness” or “difference” that is frequently bandied about when we talk about trans* folks in sexual manner, especially those individuals who are trans* feminine? If that is the case, you need to do some internal work (perhaps with a therapist? Or an educator? Or even just some good, honest friends?) to check your fear and/or privilege before you bring that further into your partner’s life. No one should have to feel as though they need to convince their partner that they aren’t scary, or different, or other. As you said, that’s your own stuff, and working through it before you take the relationship further is the most respectful thing you can do.

And if it’s something else? Marinate on it. What things can you do first to be the best partner you can be? It could involve educating yourself more about the transgender community. It could be attending SOFFA or other support groups to be able to process your stuff in a safe space. It could be working with a counselor or therapist to get to the point where you need to be. Regardless, it sounds like you’re already on the path to self awareness, and are ready to put in the time and effort to work through your existing “issues.” Hopefully, once you do, you’ll be able to really be a fabulous partner, and continue open communication throughout your relationship.

 Best of luck!