First Date Questions That Won’t Scare Him Away

Ah, the first date… That magical moment where you find out that your crush was baseless or the guy you’d tried to dodge for ages (but finally gave into because you ran out of energy) has the potential to be your perfect match. First dates are full of surprises, and while they’re not the time to dig super deep into a guy’s subconscious, there’s no reason that you can’t find out a lot about your potential paramour – not least of which is whether or not you’re actually interested in a second date!

But as all experienced daters should know, there’s a catch to the First Date Third Degree: some questions have a way of giving the wrong impression. For instance, “where do you see yourself in five years?” can imply that you’re a.) conducting interviews for the position of husband, b.) only interested in how much money he makes/will be making, or c.) any of a zillion other things you never intended the question to mean…

So how do you get the dirt without being too direct and–gasp–scaring him away before you’ve had the chance to see if you like each other? The good news is, it’s simpler than you think!

Get a Little Taste…
It may sound silly to some, but it’s been said that picky eaters make lousy lovers. Now, this probably isn’t true (generalizations rarely are), but the sentiment is easy to understand. Someone who is averse to trying new things at the table may be averse to trying new things in other places (the bedroom being only one of them). That’s just one reason why talking about food is great first date fodder.

Human beings spend a good deal of time eating. Let’s face it: in most circles, the words dinner and date are practically synonymous depending on who’s joining you! So, whether you’re a foodie or a health nut (or both!), finding out your date’s favorite foods (or at least his attitudes toward food) will clue you into your compatibility in at least one area. If he’s a five star diner and you’re a fast food freak (and proud), you may have a problem! And if he’s all meat and potatoes all the time, only one word comes to mind: missionary.

Is that enough for your delicate palate?

Take a Little Test Drive…
Different people feed on different things – emotions that is. Some of us are passion-driven, others thrive on practicality, and there’s a whole host of other motivations in between and beyond fire vs. logic. Knowing what motivated your man thus far in life will tell you a lot about the direction he’s headed.

For instance, if he became a lawyer because that’s what his mom and dad wanted… but he seems to actually love the practice, it’s quite different from begrudging his parents for pushing him into the family business and constantly contemplating ways to get out. If he’s a waiter because he loves the restaurant business and plans to stay in it for life, his personality probably differs from the aspiring artist with a day job or the guy never bothered to think much about how he gets by. And what about the guy whose sense of adventure motivated him to take a year or two off and travel the world doing odd jobs? While his paycheck may not (yet) meet the guy who cautiously climbed the corporate ladder, his life experience very probably makes up for it in other, interesting ways (depending on who you are and what you want, of course).

In other words, motivations will often tell you a lot more than situations, so ask him how he got here… Why did he decide to move to Wisconsin/get into real estate/become a certified scuba diver? (Whatever you’ve found out about him can come into play with this question.) Knowing the engine that drives your date – or at least one of them, gives you a peek into his future behaviors and his general way of approaching life. But be honest with yourself about what you hear – after all, what sounds romantic now, may not be down the road. And even if it is, it might not fit into the life you want for yourself. Then again, it could be just the welcome change you’ve needed.