What Questions Should I Ask a Man on a First Date?

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A date should be like an interview. At least, you should think of it as an interview. The guy should think he's having a good time. This is the same whether you are a man or a woman. However, if you're a woman, the importance of vetting your dates through the interviewing process is even more important. You want to quickly and easily identify the freaks, wife-beaters, dullards, and others who you wouldn't normally give the time of day.

That being said, a first date should also be light, not serious. Thus, ask these questions casually and in the flow of normal conversation. You're not supposed to sit there with a laundry list and an interrogation light.

Here are some good questions that will let you know whether a second date is worth your time.

Do you like to do the talking or be the listener?

  • Talker
  • Listener
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  • Where do you see yourself in 3, 5 or 10 years? - Pick a time period that's relevant to you. If you're in your 20's, ask the 10 year question. If you're in your 30's or 40's, maybe ask one of the others. It's important to know that a man has a plan and that he thinks about the future because, trust me, some men don't think about the future at all. They just see themselves drinking beers and playing video games until they're 80. If you want to be that harpy who ropes her man into having kids and a career (or just hangs out with her occasionally) so he can tell his buddies what a whip-cracker you are, go out with a man who doesn't think about his future. And I'm not saying you have to marry the guy, but men who don't think about their future or worse, can't answer a question about it, aren't worth your time. There's got to be some kind of plan, even if it is a small one.
  • If I called your ex-girlfriends, what do you think they'd say about you? - Believe it or not, this is a good conversation starter, though you want to be careful about implying that you're looking for a boyfriend if you're not. Good guys don't kiss and tell, but you'll learn a lot by the way he responds to this question. A crafty way to get him to talk about such things is to do it yourself first. A guy who's got nothing to hide will not be the least bit offended by this question. Certainly not every one of his past relationships necessarily ended well, but if his exes think he should be in jail, you might want to run.
  • How much time do you spend watching sports? - If you like sports a lot, then this is not a problem. If you want to spend your weekends doing something other than watching sports, then you might want to figure this out quickly because it can be a sore spot for a lot of women. Hopefully, you know something about what happened over the weekend and can broach the topic by mentioning something about a game. If not, do some research on ESPN.com and bring up a subject. See how much he knows about it. If you find out you've just met a guy who thinks the television is his best friend, you should move on.
  • Are you into video games? - This is another area where you might want to do some research. Does this guy own a video game system? If so, you might be falling asleep by yourself a whole bunch because guys who play video games disappear for hours and sometimes days at a time. You want a guy who wants you more than he wants to blow imaginary stuff up.
  • Have you ever been in a fight? If so, why? - It's important to get an understanding of how a man views violence because many men resort to violence as a means of dealing with problems. Does this guy take pride in the fights he's been in or is he apologetic about them. Maybe he hasn't been in any at all. You're trying to find out whether he's a lover or a fighter.
  • What's your dream job? - You really want to get a sense of what a man thinks is success, particularly if you are a professional woman and don't want to introduce your date/boyfriend/husband as "this is Joe, who sits at home in his pajamas all day and plays video games while I'm out working." Also, it's just a fact that successful women want to be around successful men, so if you're not a successful woman, this question matters less to you unless you expect a certain standard of living. It's also a fact that we prefer a man who makes more than we do. Certainly, not all of us, but a lot. So if your man's dream job is to work in a marijuana dispensary and you're looking for a high standard of living, you might want to rethink things.
  • Who's your hero? - This is a good conversation starter and will tell you loads about a man. Is his hero somebody who's a sports figure, a historical figure, or a personal figure? Is this man shallow or does he have depth? A man who answers "Michael Jordan" is a lot different than a man who says "My mom, because she raised me and my brother by herself and we were always happy." An interesting man is going to have an interesting answer to this question. A boring man is probably going to have a boring answer.

  • What's the funniest movie and television show you've ever seen? - If there's physical attraction, the next thing to find out about is his sense of humor. This question is easy to ask and will give you a sense of whether you and the man think that the same things are funny. Obviously, if he thinks that "Death Wish" and "Twilight" are hysterical, you'll probably want to quickly exit your meeting place. But if he starts talking about your favorite funny movie and his whole face lights up, you know you're on the right track. There's nothing sexier than agreement.
  • If you could know one thing about me right now, what would it be? - Guys with no class will say something so stupid you will be able to right them off immediately after asking this question. A guy with no class will say something like "if you're going to sleep with me" or "whether you're shaved or not" or "if you like threesomes." A guy with class will take a moment to think and say something simple like "what's your favorite color" or "whether you prefer roses or carnations." This question is designed to separate class from classless.
  • Tell me about the guys you hang out with the most. - Contrary to some popular opinion, we women want and needs a guys who have friends. We do not want loners and/or guys who don't have friends because people with no friends are generally friendless for a reason. Besides, regular guys need guy time in order to be happy and if they don't have an outlet for guy time, they're likely to be miserable. In addition to that issue, it's good to get some detail on a guy's friends. The kind of guys a guy hangs out with will tell you a lot about the guy. It's really an indirect way of asking a man about himself.

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