How to Meet Shemales

by Alec Jaye, Your Shemale Pick-Up Wingman

Shemale pick-up tips with Alec JayeHow to meet shemales is another one of those most frequently asked questions. It isn’t as difficult as you might think, although some guys claim to have no luck at all. We’re going to change all that. If you haven’t already done so, I highly recommend that you read my article “where to meet shemales.” I have covered where to meet shemales in depth so let’s chat a little more about how to meet her, how to approach her and how to make a great first impression.

Seriously guys, I’ve seen some of the approaches guys use. They are far too forward from that first meeting. I’ve seen guys grab her crotch at first meeting, or start making obscene statements. Do you want to scare her off or would you rather make a first impression so you have a chance to meet her, chat and possibly score a date. That’s really what your goal should be. Meet a shemale, have a nice, pleasant chat and then get the date. Whatever happens after that is the proverbial icing on the cake!

How Do You Meet Shemales?

Let’s recap some of the fastest way to meet shemales both online and in person. Meeting shemales online is perhaps the fastest way. Even if you pay a site membership fee, it’s going to be a lot cheaper than hanging out at the bars and nightclubs. Anyway, you can meet shemales in online chat rooms, trans sites, social media sites and shemale dating sites. Until recently classified ads such as Backpage.com were a great way to meet local shemales. With the proliferation of human trafficking that is no longer a good option. Many of the escort sites have been shut down and law enforcement is actively running sting operations. Regardless, the internet is a goldmine for meeting shemales that are nearby and interesting to you.

You can also head out on the town. This is much easier if you live in or near a large or mid-size city that has an active LGBT community. Many gay bars welcome shemales. Some cities will have bars or nightclubs that cater specifically to the trans community. These are great places to meet shemales. You might also want to do a Google search for transgender social clubs in your area. Many will have parties and social get-togethers you might be able to attend. If there are transgender support groups or clubs in your area, a little research may reveal the places and activities where you may be able to run into them.

For an in-depth look at places to go, see my article at where to meet shemales.

So You’ve Met a Shemale and Want to Ask Her Out On a Date

Nice job! You’re doing something right. You’ve met a shemale and it’s time to ask her out. I believe the key is to be respectful. Don’t be a wuss! But don’t be a creep either. Make a nice introduction. Ask if you can buy her a drink or ask a polite question. OMG, don’t ask if she still has a dick! Spend a little time chatting and let her see your charming personality. Be sure to listen at least as much as you talk. You know, all the usual stuff when you meet any other woman and want a date, or a hookup. Unless you’re paying for a service you’re going to have to work your way into it.

I just recommend a direct approach. Think about a nice date and ask her if she would like to join you for coffee (or dinner) at a local place. Use your imagination but make it some place where you can chat in a relaxed environment. I have found it’s a great approach to start with coffee. If it isn’t going well you end with the coffee date. If it is going well, ask her to dinner. She will probably say yes if she feels the same way as you. Then, if you’re both feeling it, you can go out on the town and have fun, and see where it leads. Treat her right and you may end up with mind-blowing shemale sex!

What About Rejection?

Short answer. Don’t take it personally. You just didn’t click. Maybe she is insecure and not ready for dating. Perhaps she has a boyfriend already. It’s possible that she’s a heterosexual crossdresser who isn’t ready for the attention of a man. It could be any number of things so don’t read too much into it. Her loss anyway, right guys. Move on and try to learn from the experience. Did you feel awkward at any point? Did you feel you could have said anything better? Rejection isn’t fun. I’ve never really had a really negative rejection. I like to think it’s because I keep things light-hearted and fun during that initial interaction.


Ok guys. You know how to meet a shemale and the basics of how to approach and attempt to take the next steps of a date and possible romance. I’d love to hear about your experiences.