Dating a trans woman is not that different than you might think. You’re likely feeling more awkward about it because you’re worried about doing or saying the wrong thing.
If you’re heart is in the right place and you are respectful, a misstep or two isn’t the end of the world.
Tips for Your First Date with a Trans Woman
Don’t focus on her being transgender. You may find trans ladies attractive for all sorts of reasons—their strength, their beauty, and their journey may be things you are drawn to, but her transgenderism is only one, albeit important, part of her. She doesn’t want to be fetishized for that.
Treat her the same as a cisgender woman. When you find yourself going down your rabbit hole of insecurities, wondering how to behave or what to say or not to, just remind yourself of how you prepare for a date with a cis gal. Relax, work out, listen to music… do what it is you do.
Compliment with sensitivity. Most women do love compliments on how they look on a date because they usually put that extra effort in, so go right ahead and tell her she looks good or beautiful or sexy. The only caveat here is not to add something like “… for a man.” or “I can’t believe you were a man.” Keep these thoughts (if you have them) to yourself.
Ask lots of questions and listen attentively. It’s rude to spend a date talking about yourself. Show her that you’re keen by asking her about her life. Stay away from trans-specific questions unless she steers the conversation in that direction. Her family and friends and pets, her career and goals, her passions and travel are just a few things you can inquire about.
Let her set the pace and be flexible. You may not know and be wondering how far along in her transition she is, but don’t make that your focus or let it be a distraction.
Most trans women will want to take it slow either because they want to know you are into them and not their transgender experience, and likely because they’ve had to put up with insensitive men who either fetishize or who are ignorant. Don’t be that guy! Make the move when you’re sure she’s into you.