How to Flirt with Trans Women You Meet Online

Men often ask me about flirting—when to do it, how much to do it, but mostly just HOW to do it?

Flirting is the foreplay to foreplay to sex. It’s usually part conscious, but often subconscious when we’re attracted to someone (and sometimes even when we don’t feel the connection right away).

Flirting should be fun and light and playful. The key is not to overthink it.

When you meet a beautiful trans woman on a dating site, you can engage in light flirting immediately in your first message. Be sure to read her whole profile first, and then craft a personal message that will reveal that you’ve read it and think there is a possible match between you.

A sense of humor can go a long way with flirting—with a quick wit, a little self-deprecation, and a cute joke, you can make most women smile and hold theiur attention.

Be mindful though that she may have a different sense of humor—what one lady finds a riot, another might find gross. Be cautious until you actually meet in person.

From a woman’s perspective, we can usually gauge a man’s depth and breadth of humor from his profile (which shouldn’t be all jokes, by the bye). We want a man who is fun but who can be serious when he needs to be.

Teasing is also part of flirting and is something that can spark playful banter. Just don’t overdo it, as some women are put off or offended by teasing. If a woman likes dishing it out, though, she likely won’t mind taking it.

Compliments are another form of flirting. You can do this as you find out about her personal goals, interests, and achievements. Tell her what turns you on about what she does, before what she looks like (not to say, most women will appreciate when you notice the effort she’s put into looking good for a date).

Once you do meet in person and have had a few dates, you can ramp things up if you feel the connection. Games—whether board, video, or something more physical—are a natural setting that encourages teasing, playful trash talking, and a competitive spirit (all matters of flirting that will help you get to know a person while having fun).

If you do feel the lightning-bolt chemistry, you can add a sexual edge to your flirting, but only when you feel it coming from her too. I always suggest letting a woman take the lead when it comes to sexy flirting (mirror her behavior) to play it safe.

Remember, flirting isn’t some magical technique reserved for casanovas—it’s just about paying attention, being genuine, natural, and respectful of women you are attracted to.

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