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timmy
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Has no life at all |
Location: UK, in Devon
Registered: February 2003
Messages: 13796
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There he is. He looks nice. He's everything you find attractive. He's got a lovely voice, he's as manly as you want, or as androgynous. He's the right height and weight. He smiles nicely. You know him well enough anyway because he is in your school/ work /social set. But you have no idea what his thoughts are about gay folk, nor what his sexuality is. All you know is that he is at home, socially, with male and female, and he is comfortable enough in himself to flirt, or look as if he is flirting, with male and female equally.
You and he have shared coffee (etc) socially anyway, either alone or in a group. You are on speaking terms, at the acquaintance level.
You are not out. No-one has, as far as you can tell, any idea that you are not heterosexual. Coming out would be viewed fairly neutrally where you are though there will always be exceptions, but you have not yet chosen to do so.
What now? How do you ask him on a date?
Author of Queer Me! Halfway Between Flying and Crying - the true story of life for a gay boy in the Swinging Sixties in a British all male Public School
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Hmm, Timmy...are you seeking information on a personal level or hoping for an educational response for the readers? 
I have always thought that mano a mano, guys have it easier in developing the information necessary to determine an answer to your question. In the straight world dating has such strict overtones.
I remember conversations with my male freshman students about dating at the college where I worked. Yes, I enjoyed watching many of them squirm, but it was also a good way to bring out the closeted ones for mentoring.
"In High School dating has less meaning, it's more about learning the ropes on how relationships work," I would say. "College is a different game, for here a young man is evaluated as a potential life partner." Used to scare the hell out of some of them.
Of course they all assumed my discussion was heterosexual in nature, but I always remained neutral and could tell which ones understood that point.
So men can use activities as a safe dating exploration. Viewing games of sport, fishing, camping...none of which seems like a date, just friends. There are no expectations as there would be if the companion were female, just guys out having fun.
Perhaps this would be the point that a keen sense of perception would allow the youth you described to be evaluated, observed and found out. Conversation in a buddy situation is much more open, less confined to the tradition gender roles...and even that can be discussed.
The perception of flirting is a good place to start, although we don't often know how sensitive the other person may be to a reaction. That response line of "Are you coming on to me?" is more likely to fall flat than any other.
It takes courage to stand forth as gay to someone who is part of the unknown. If you are not secure enough to be out then probably neither is he. I have had self depreciating students tell me that they did this or that, followed with "Oh, I know, that makes me seem gay." Well, yes it does, and what a good way to open a door to further admissions.
I don't think you can ask another guy on a date when the truth about yourself remains hidden. It would be best if you are open about your feelings, or at least your understanding of them. If you are not out then how clear are those most intimate details anyway?
And if the response is "But I'm not gay." Then if he is willing to accept a friendship without feeling threatened then maybe he has a cute younger brother or a friend he might let you know about. The idea is to come away feeling like a winner. 
Age appears to be best in four things; old wood best to burn, old wine to drink, old friends to trust, and old authors to read. (Sir Francis Bacon 1561-1626)
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How do you ask a boy to go on a date? 
