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Tips for Planning a First Date with a Trans Woman

Couple Crossing Ladder Bridge

Like everything associated with online dating, you get what you give. If you haphazardly join a dating site to meet trans women, write a couple sentences in your profile and post one blurry pic, you’re probably not going to get any messages. Likewise, if you send one-liner first messages that are overtly sexual, you probably won’t get any replies.

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Sometimes I feel like I’m beating the same old drum here, but hey, if I can help just a few men out there, I’m happy. So let’s assume you are getting messages and replies, and you’re onto the first-date stage of things.

Most women don’t like surprises, especially from a stranger, but the surprise here will be the idea, not waiting until the night of to tell her. When you do come up with your plan, I recommend having a backup for insurance. And if she disappoints you by passing on A and B, be flexible and go with the flow. Remember, you really don’t know this woman, even if you’ve been messaging back and forth online for some time.

All your helpful cues will be right in her profile, as well as through those back-and-forth online conversations. Play private investigator and read between the lines. She may have written a laundry list of her interests and activities that she enjoys, but it may not be that obvious. Of course, you have things you love to do, but put her first on the first date.

Some of you will be saying this is all too much, the ones of you who are just looking for a hookup. Bah, I say, all women, even those only interested in casual dating, want to be wooed and treated like a lady. And you are far more likely to get in her pants or up her skirt after a fun thoughtful date.

Whatever setting or activity you do choose, keep in mind that a trans woman will also want to feel safe with you, in an environment that is less likely to attract discrimination or unwanted attention.

One last thing: I think a man should plan the first date and pick up the tab, but if your date feels more comfortable planning and wants to go dutch, let her.

Share a memorable first date in the comments? What made it special?

Tell us what you think!

Tell us what you think!

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