A
male
age
,
anonymous
writes:I need some good advice! I'm a gay 58 year old male who is quite attracted to a young 23 year old guy. We've been friends ever since he was a little fellow. I believe he is gay but I'm not 100% positive about it. We're planning to take a trip together in December (he actually approached me about sharing a room for this) and I'm hopeful we'll be able to have a most enjoyable time. He appears to be one of those rare young persons who is quite comfortable with older folks. I certainly don't want to lose his friendship but how can I find out diplomatically if he is gay or not? All of the indications I get seem to indicate he knows I'm gay and that he has no problem with it. To just come right how and ask if he's ready to hop into bed seems a bit risky to me. Advice? Reply to this Question
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female
reader, anonymous, writes (11 August 2007): Why do you seem to think that if he does turn out to be gay that it automatically means that he will hop into bed with you? I mean he might be gay, but just because he is doesn't necessarily mean he is going to be interested in you. But for your sake I hope he is. Anyways, I am a very straightforward person. I would just ask. But I have lived in nyc for six years, and culturally here, that is not an offensive question to ask anybody. I have been asked crazier stuff. I was at a bar once and this straight couple, they were pre med students, asked me if I wanted to do a threesome with them. Even though I never would, I wasn't offended. Just ask.
A
female
reader, AskEve  +, writes (11 August 2007):
 There's still 4 months to go till you take that trip with him so make it your point when you're in his company to talk about some gay issues. If you know each other as well as you profess then this shouldn't be a problem. Has he ever had a girlfriend in the past? Do you see him looking at other guys? What makes you think he might be gay?
The only problem I see here is the age difference. You are 35 years older than he is which is quite an age gap. You're from totally different generations and I think this will cause problems. Knowing him all his live, your relationship with him might be perceived by his family as a friend only, anything more might be seen as predatory so be very careful here.
Eve
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A
reader, anonymous, writes (11 August 2007): All I can say is - DON'T ASK DURING THE TRIP. It would just be painful to be stuck with him if it, for whatever reason, went badly. If you two really are such special friends, he'll let it slip out sooner or later. You can just be patient in the meantime. If he hasn't already blurted it out he may have reservations which you need to respect. There's nothing worse for a closet-case, or even someone in questioning, than having someone else quiz them even in the most diplomatic terms. If you feel you must nudge him slightly, you can talk about queer issues or some of your experiences coming out, but don't force the issue.
Even if you assess if he's gay after all, you should also consider if you're not mistaking his friendship for romantic interest. If you've known him since he was a child, you probably have a very intimate bond which could (if not scrutinized carefully) be just a deep friendship. Don't chance that if you aren't 100% sure he wants to date you.
You're working against a pernicious stereotype of older, predatory gay men, so I'd advise you to let him make the first moves.
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A
female
reader, bee-ess-2007 +, writes (11 August 2007):
 if he is a good friend
im sure you could say u were concerned about him
and make him understand more why your asking!
i mean his sexuallity may be private to him... but if you are close he should be open and honest to you!
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