Q: I've told men up front that I'm male-to-female trans (I date straight guys), and I've also waited until longer into the relationship, and I still don't know which is the better approach. I don't want them to be disappointed (or to lose their attention), but I also want them to know I'm an honest person—someone you could have a relationship with. What's the best strategy for this if I'm looking for a keeper, i.e., not just sex?
A: Whether and when to disclose that you are transgender is a personal decision, so there is no right or wrong here. It's a private fact about you that might become relevant to someone you're dating if the relationship progresses past a certain point, but it's also something that you don't owe other people an explanation about.
Some trans people prefer to be open about their transgender status in all aspects of their lives; others prefer to disclose it only under certain (safe) circumstances, and many folks fall somewhere in between. In the past, many transgender people received advice from health care providers that they should keep their trans status hidden at all costs. Today, however, there is a growing understanding that it can take a heavy emotional toll to feel obliged to conceal such an important aspect of a person's life.
In light of that, here are some considerations that might help you decide what feels like the right choice for you. Let's say you decide not to say anything early on, what could happen? You may end up spending more time and energy feeling anxious about when you will disclose that you are trans and how the other person might react. With that in mind, if you disclose your trans status up front, you can avoid wasting your time dating anyone who does not accept who you are or who would feel deceived. It can be hard to talk about something personal, like being trans, with someone new, but this is a pretty big payoff.
Regardless of when you tell someone that you are trans, be aware of your safety. It is sad but true that violence against trans women in the dating context is all too common, and it can be hard to know in advance whether someone is prone to violence. If you have any cues that he might be—say, if he seems to be homophobic or controlling—be extra careful. But no matter what, make sure that you are able to get help and support immediately if you need it, whether from your friends and family or from local LGBT or antiviolence organizations.
Q: My best friend Marc is a champ at gay speed dating and thinks it would be great for me, too. Honestly, the whole thing intimidates me: all those guys, so little time. He wants me to go with him to one that promises 10 to 25 dates in an evening. Isn't this completely superficial? And more important: What should I wear?
A: Speed dating has become very popular lately. But the first few times are nerve-wracking for most people. Try not to feel intimidated but do think ahead about some questions to ask, because it's easy to get tongue-tied knowing you're being judged while the clock ticks away.
Steer away from questions that will result in a yes or no answer, since they won't get you into the rhythm of a conversation. Ask about things that matter to you: "What kind of work do you do?" for instance, or "Where have you vacationed recently?" Try to avoid especially involved questions, like "What's your relationship with your family like?" or deeply personal ones, such as "Top or bottom?" Some people even jot down questions on a slip of paper. Remember, you should be asked questions, too. If one of you is doing all the talking, it's time to move on.
Keep in mind that speed dating isn't for everyone. But all you really have to lose is about $20 and an evening. And some people really do make great connections at these events.
As for what to wear, put a little extra effort into your look. If any dating scenario is about first impressions, this is it.
Q: Even though my lesbian daughter can't marry her girlfriend, Lisa, because it's not legal in our state, should I treat Lisa as I do my other sons- and daughters-in-law?
A: It all depends on your daughter's relationship with Lisa. If she is a casual girlfriend, then no; she doesn't have the same status as a son- or daughter-in-law. But if they are in a committed partnership—regardless of the legal basis—yes, do the right thing, even if state law doesn't.
Steven Petrow is a regular contributor to The Huffington Post and Yahoo! He's also the author of The Essential Book of Gay Manners & Etiquette. Ask him your own question at email@example.com.