#solitair-e

I've done this kind of thing before, but I'll try to explain the best I can without having seen your family member first.

This might not work as well as it sounds – I think the best strategy is what some people call "tactics" or "adversarial approaches." What this means is that I suggest some of these strategies at the outset, and they may or may not work. Then, when the time comes, I don't say anything and see what happens.

If your family member is someone you talk to regularly, then the key thing is to talk to them in a way that lets you feel confident. If they have good things to say, then they'll be happy to have the chance to discuss your coming out with you. If they're not willing to listen to you, then I'll still give you the option of coming out to them privately, with a few disclaimers:

You're absolutely not obligated to tell them if you don't want to.

You are allowed to tell them that you will come out to some people but not others.

You can come out to anyone you've told of it before (or might come out to); if you haven't come out to a given person already, it is okay to say so right now.

You can come out to someone at any time you want, or you can come out to one person later than that, or you can come out to several people at once.

If you don't have regular interaction with them, the key thing will be to look for information about their attitude toward LGBT people. For some people, this can be easy – it's obvious from the way they talk that they would be okay with it, and even if you see them say something in a "contrarian" way that would make you second-guess whether you should come out, you can go ahead and let the issue go and see what happens.

But for some people, it's harder. They could be the kind of person who talks "contrarianly" even about noncontroversial topics, or who gives you weird and not-helpful responses to questions. If they make you uncomfortable, they could be unpleasant or even dangerous to be around; on the other hand, their behavior could be easily misunderstood (as one of my close friends has recently discovered). In those situations, it's a balancing act of finding the right balance between being cautious, and being determined enough to get the right information.

In general, you may want to try to get information from other sources. Talk to LGBT-oriented people or groups about your family member, and find out what they think about them. If there is information out there, you may also want to talk to them to find out if you should follow it. Be aware that people can be unhelpful, but you have to consider the cost of that unhelpfulness.

I'll give this one the benefit of the doubt and assume the most charitable interpretation possible.