Honestly, finding out a trans person’s sexual orientation is the same process of discovery that it is with a non-trans person.
The only difference is that, if a non-trans person is at an event that is specifically organized for LGBT people, you can usually (but not always) assume that the person is a gay man or a lesbian. A trans person at the same event might be a gay man or a lesbian, but he or she might be straight and be at the event because it is trans inclusive.
I honestly don’t know that many people who would be offended by someone asking their sexual orientation, but I’m sure that there are some (and those who are will usually be straight). Regardless, there are some things that you can do, and these are the same things that I would advise a person to do regardless of whether the object of interest is trans or non-trans.
1. Ask the person – point-blank. Say, “I don’t want to offend you, but I’m interested in finding out whether you date men or women. The reason I ask is because I’d like to ask you out.” Then the ball is in this person’s court, and hopefully you will score.
2. Ask the person out – point-blank. If he or she says yes, you’ll have your answer. If he or she says no, you might have your answer and you might not. But you will at least find out whether or not the person is interested in you.
3. Strike up a conversation about dating, exes, or some other topic that might give you a clue. For example, when a certain song comes on, you could say, “Wow. That reminds me of my ex.” Then talk a little about your ex (or even a made-up ex) and see if it leads to this person talking about his/her ex or who he/she is dating now or wants to date. The gender of an ex is not always representative of who the person might be interested in, but it can at least provide some information.
4. Ask this person’s friend. Not only is this a good way to find out about the person’s interests, but it’s a good way to relay your interest to the person without a lot of risk – because the person’s friend is going to tell him/her that you asked. It might be a little junior highish, but so what? We all revert to awkward adolescence when we start dating someone new or want to ask someone out.
5. Look for obvious clues. Not all gay guys love Cher, but most straight guys don’t or won’t admit it. If he has a bunch of Cher songs on his iPod, it’s not a dead giveaway, but it’s close. Not all lesbians go to The Dinah every year, but most straight women don’t. If she does, or even knows what The Dinah is, it’s not a dead giveaway, but it’s close. Straight people are harder to detect, but they often have photos of hot people as screen savers. Actually, so do gay men and lesbians. So check out the gender of this person’s screen saver. That probably is a dead giveaway.
No matter what you decide to do, remember that there are no guarantees about anyone’s sexual orientation. A friend of mine approached a bouncer in a gay nightclub and asked him out. Now you would think that a bouncer in a gay nightclub would be gay, right? Well, he wasn’t. Obviously he was used to being hit on by gay men, and if it bothered him, he had the wrong job. But he did say, “Sorry, I’m straight.” And that was that.
No matter who you ask out, you take your chances – and the main risk is that the person will not be as interested in you as you are in him/her. So you might want to just grit your teeth and go for it. If you get rejected, you will join the ranks of the rest of us. Good luck!
Readers, what other thoughts or advice can you offer?