Transgender Dating: Where to go on a first date?

Posted on June 3, 2018
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You’ve decided to take a transgender woman out on a date for the first time. You have zero clue on where to take her and what to do. I’m a transgender woman and I’m going to share with you the most memorable first dates I’ve had.

PS: I have a quirky personality so I’m not sure if some of the following tips will work for you.

Movie and Candy (Beginner)

I wasn’t a virgin when I was 18 but I was a bit inexperienced with dates. I’ve only had one serious boyfriend when I was 17 and about 4 short-term intimate relationships with 4 different men. Suffice to say, I don’t want to have a daughter like my 17yo self.

From 2007 – 2008, I’ve had one date that’s so memorable to me (not my ex-boyfriend). It’s with this aviation student (he’s a pilot now OMG) who’s the same age as I was and we both didn’t have the cash to go on a fancy date. We met at Greenbelt Mall in Makati, Philippines, and I wasn’t sure if we watched Narnia or Paranormal Activity. What I remember is him looking very dashing in a dress shirt, jeans, and leather shoes (very well-dressed for an 18yo).

He was such a gentleman and held my hand whenever we walked. He bought me candy because I’m not a popcorn gal. It was magical to me because I didn’t care if he’d take me to an expensive place. I was 18 and I just wanted to have fun.

What I’m trying to say is that you don’t have to do a lot of things to impress a girl. Just look good, smell nice, and be a gentleman. He complimented me as soon as he saw me so that’s vital if you’re taking a transgender woman on a date. I was wearing heels and it pinched my feet so I better get some credit for it.

Wine Bar (Intermediate)

I’m in no way an alcoholic but I thoroughly enjoyed my experience from my wine bar date. I think I was around 20yo when a 30-something guy took me to Barcino in Greenbelt. He was cultured and well-traveled so it was really nice to taste stuff for the first time.

I think the novelty will not wear off in regards to wine tasting so it’s a good first date destination with a transgender woman. Some may get offended because they might think that you’re trying to get them drunk but I think it’s a lovely place.

I especially liked how cozy we were together in a lounge and the wines helped us both to be more open and talk. The place was romantically lit (not too bright) and is the perfect setting for a first date.

Theme Park (Amanda’s Favorite)

Technically, my theme park date wasn’t a first date with the guy I went with. I’ve had sex with him the night before so the jig is up. I’m very competitive when it comes to games and I like going on adventures so Theme Park is the perfect place to take a transgender woman like me on a date. Going on a theme park will entail a lot of activities and will truly measure one’s interest for the other. We both spent hours riding different rides, getting wet, playing games, and entering “dungeons”.

Never did we both get pissed off at each other and we shared truly amazing moments that live with us up to this day. He was a bad lay but he’s an amazing date. The theme park experience made me give sex a try for the 2nd time with him and… it was still bad. The point is, no matter how disconnected you feel with each other, a theme park can somehow evoke romance.



About the author

A cross between a couch potato and a finishing school alumna. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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