What we really wanna know when we’re pummeling our first date with questions is, “Does he like all the stuff I like?”, perhaps even, “Does he have all those qualities I fantasize about?”…
Thus first-date Q&A’s are obviously very subjective. Perfect example: I, personally, would never ask a first date whether he’s into sports because sports aren’t part of my life, so it wouldn’t cross my mind. I may, on the other hand, ask him what he reads (the real question I’m asking, of course, is “Do you read?”…)
But there are, universally, details we should want to know—because if we’re at all serious about an ongoing relationship, the answers could sway our decision-making.
These are questions you’ll wanna squeeeeeze in somewhere along the way. Once the first is on the table, the ice’ll definitely crack. Depending on the answer you get, hopefully you can relax about having to ask the rest.
Where do you work? Not “what kind of work do you do?”, but “where?”. If you ask this early during the date, it’ll sound like small-talk. If you save it until you’ve already learned a bit about the guy you’re sitting with, you’ll have a better context for his answer. What you’re looking for is this: is he an unemployed deadbeat?
Are you married? There’s a never-ending flood of gay guys in straight marriages who are looking to get their secret ya-yas out. No matter what you’re “promised”, these guys are far from being in a position to offer you anything substantial—tell them to hit you up once they get their shit together. If your date is in a same-sex marriage, determine whether or not it’s an open one: being part of a lie sucks.
Have you ever been married? I think it’s fair to know if there’s an ex-wife in the background. An ex-husband might have less drama, if you’re lucky, but at least they aren’t part of a package-deal with kids. Which leads me to…
Do you have kids? If so, what role do they play in his life? How often does he see them? Does he seem like a loving father, or does it strike you that he finds his kids to be a nuisance to his new gay lifestyle? The answers not only reflect his character, but can be a red flag to you if kids aren’t in your cards… even for a weekend.
You’ve never been arrested, have you…? I have no problem pulling this one out. But I usually only do so when I’m on a date with a guy who seems so TOTALLY perfect that I begin to suspect something MUST be wrong with him. The answer is likely (and, for me, has always been) no, and you can have a good laugh. If the answer is yes, well, you’ll be glad you asked…
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