While women who have been born with female organs might have complex feelings about being treated “like a lady”, there is nothing wrong with trying to be a gentleman on a date. If you have the good fortune to be able to ask a trans woman out, here are some ideas to make the date romantic and to make her feel special.
1. Open doors, and pull back chairs. I know this is old fashioned when it comes to modern dating, but it never hurts to try it out one time on a date. If she seems to respond to it with a smile and a sincere thank you, then it is probably helping her to feel special.
2. Compliment her. When you greet her, tell her she looks lovely. It wouldn’t hurt to tell her again during the meal, maybe as you are clinking wine glasses. Just say: “Here’s to you. I’m honored to be out with such a lovely woman.”
3. Ask her to dance. It doesn’t matter where it is, or what the music is. I once asked a woman to get up and dance with me at a Chinese restaurant in the middle of the day, while some strange flute music was playing. The gesture is what’s important. Spontaneity can be very charming.
4. Assume that she is a woman. Don’t go on about transitions, or surgery, or hormones. If she brings it up, then by all means talk about it. If she doesn’t, just look into her eyes and talk naturally about life and love. It’s nice to feel comfortable with someone and just chat.
5. Listen to her stories and don’t always follow up with stories about your own life. Instead, ask her questions about her story and try to show interest in her life and her experiences. Talk with her, don’t talk at her.
6. Steal a kiss. It’s always hard to know if someone wants to be kissed or not. Sometimes the vibe is obvious and sometimes it’s unclear. A lot of people say the ¾-rule is the best. If you lean in ¾ of the distance between your faces then she will come toward you for the last ¼. The last part of the date before goodbye is usually the time I pick to steal that kiss. This way she knows what I intend, and she can think about it before making another date.
7. Don’t assume that a trans person is going to have sex with you on the first date. This is the same for everybody. It is a fact that if someone makes you wait a little, the relationship is going to last longer and stay stronger.
It’s good to treat anyone with respect, make them feel special, and make them feel beautiful. If you get a date with a trans woman, be nice and have fun!