The absolute best option - but also the least likely is meeting a transsexual woman at a typical straight club, tavern or social setting. There’s a large number of transsexual women living and operating seamlessly everywhere - particularly in larger cities.
Lots of transsexual women prefer the idea of meeting a man where the fact they’re transgender wasn’t why he sought them out.
Additional chapters Included in this section on this subject, include:
Connecting with a TS at "straight" Venues
The Dreaded First Phone Call
Meeting at Transgender Friendly Nightclubs
First Meeting with a Potential TS Partner
Also, her “tranny guard” is usually down in these environments. In typical dating mode? She’s all too aware many guys are just seeking a perverted trip versus a meaningful union. Also, anytime we first encounter someone in a social setting it gives us a chance to get to know them better - without visual prejudice. Thus, if you’re carrying extra weight that she might not find appealing with on-line photos - she might relish your fun personality and engaging smile and never notice the physical attributes.
Some transgender women much prefer meeting men outside any realm of transgenderism including my friend Lisa - a lovely and successful 33-year old transsexual woman living in New York. “I never get on transgender dating sites or visit establishments tagged as where transgenders hang. Alas, most of the guys I met at such places were either secretly cross dressing or pursuing a fantasy of having a passable transsexual woman be a “top” for them sexually – neither situation was for me. I much prefer to encounter men in straight environments & deal with the subject if & when we find some common ground. I suspect some knew before I told them – I’m not flawless. However, most didn’t seem to know & only a few cared once I revealed my transgender history”.
What’s the big challenge meeting a transsexual during everyday life? There’s four obstacles to overcome:
1. You must become exceptionally skilled at spotting a transsexual in public.
Most of us lived full time as women for many years: we aren’t easy to detect at a glance. However, guys attracted to transsexuals usually become very talented at spotting trans-women. Still, you might be wrong: I’ve known more than one born-woman with deeper voices and larger hands that’s been perceived as transgender.
2. It needs to be in an ideal social setting.
If you notice her shopping at Macy’s and start following her? Well? That’s very creepy, unsafe and usually results in a monumental turn-off. Hitting on a TS woman at her job is usually not a good situation for either of you. Likewise, you might meet her at a fun tavern - but she’s with friends or a date. Thus, just because it's the perfect place doesn’t mean its the ideal circumstances. I talked with one guy who first encountered his TS girlfriend at a local nightclub - but it took almost a year of going back before he finally met her in a circumstance where they could talk. They’re together to this day.
3. You need to let her know that you know - without offending or outing her.
This is sometimes tricky but crucial since a lot of trans-women pass on potential dates when their pretty sure he doesn’t know and they doubt he would be accepting - like my friend Cat: “When I was single and dating guys, I can’t begin to count the number of men I encountered that although I enjoyed their company - I never allowed further contact, etc. Why was that? I didn’t want to get “outed” in one of my favorite hang-out places. Granted, a few people there were aware I was a transsexual - but most were not.”
If a TS woman met and liked you at crowded nightclub? She was probably immediately looking for signs you already realized she was transsexual. However, it’s unlikely she’ll disclose this in such a bar for fear you might out her to other patrons in a derogatory manner.
If you met and chatted with a transsexual at a bar and she wasn’t confident you “knew”? She’d rarely provide you further contact information because she just doesn’t want the potential hassle. However, sometimes? If the connection you shared seemed extraordinary? She might take that chance.
How do you open the door without causing problems for either of you? It’s a good idea to try and pull away from the crowd so you can speak more freely. Imagine if you felt you needed to share with a new dating interest that you have Herpes. Would you want to share that in a crowd while screaming at the top of your lungs just to be heard? No, I don’t think so. :)
Using comments that make it clear you’re very accepting is a good way to open the door for discussion. Comments like: “I’m very comfortable with my sexuality” or “I don’t care about a woman’s past - only who she is today” - are ideal cues to let her know you’re cool with everything. Another idea? When asking how often she comes to the particular place you just met her, ask if she’s ever been to a particular bar in your area where trans-women sometimes frequent. Some guys ask if the girl was ever a performer. That’s tricky - since some transsexual women get offended by being associated with DRAG performers.
Remember…if she’s into you? She’s actually wanting to see if you know - so it usually doesn’t take much to make things open up.
4. Your both must be interested
Almost forgot this essential ingredient. She’s got to be into you, as well. Lots of trans-women have a particular type of guy that most does it for them. Thus, all your hard work might be for naught.