TS Dating

How to Fix an Awkward First Hookup

Sad Woman Lying on Bed

Sometimes you both see stars when you first hit the hay together, but hookups can be awkward.

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Maybe your signature moves fell flat this time, or maybe you acted too nonchalant so she wouldn’t know how nervous you were. Maybe you said all the right things with your last transgender date, but your t-girl this time didn’t react the same way.

Relax! First dates or first sex encounters don’t always go the way they do in the movies. Here’s how to improve your chances of a second chance if the first time fizzled.

Understand that you have to give things a chance.

You might be disappointed in how the date went, but if you like her and are attracted to her, she might like you too.

Unless she said “thanks anyways, but the chemistry just isn’t there for me” or “go fuck yourself,” give things another go by making yourself available. Things can be awkward until you get to know each other a bit.

Tell her that you want to see her again.

You want to see her again, but how will she know that if you don’t tell her?

In my experience as a woman, and talking with my transexual and cis friends, she may not even be aware that you felt your game was off or that anything was wrong. She’s wondering why on earth you haven’t called or texted.

Even in modern society, most women are going to leave it up to you to ask them out again. The biggest way to get a second date or hookup is by asking! If you don’t ask, she’ll assume you don’t want one.

Acknowledge or apologize for the situation.

Depending on what happened or didn’t happen during your date, you can respond by ignoring the situation, acknowledging it, or apologizing.

If the reason your date wasn’t perfect was because she was nervous or didn’t respond the way you hoped, don’t mention it. Just say you had a good time, and ask her out again.

If it was your doing, just say so honestly. “I came across a little standoffish because I was so attracted to you and didn’t want to act wrong, but it came out all wrong” or “I don’t have a lot of experience dating trans women and wasn’t sure what to do—that’s why I didn’t go further. I’d really love to see you again.”

If you did something wrong, apologize. Tell her why—it was a mistake, or you were too excited, or whatever it was. Don’t dwell on it, just offer a sincere apology and move on.

Tell us what you think! 1 Comment

  1. janedon1

    April 27, 2019 at 10:20 am

    Honesty DOES go a long way. Like (I’d say most) CIS girls, I expect men to be men and take the lead (at least at the start). Tell me what you’d like, maybe compliment me. Humor is always good… make me feel Fem. Unlike what some would say, I love men to be touchy feely (makes me feel desirable). I know it’s not politically correct, but that’s how I feel. When men (even if I’ve just met them) tell me I look sexy, I just feel special. But I don’t want them to mention me “manhood.” I want to be female only, a submissive female.

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