10 Questions to Ask a Guy On a First Date

First Date

One of the more difficult—and sometimes awkward—moments for every person is that first time you meet up with a complete stranger for dinner or a drink, and are fully committed to sticking around for long enough without being rude. Yep, I’m talking about a date. And while going out with someone that first time is both exciting and fun, it can be a lot of pressure to make sure that conversation is steady, with no strange pauses or moot points. As someone who likes to talk to absolutely everyone—no, seriously, it’s a problem—I figured I would give some pointers on exactly what a girl should ask a guy whenever they are sitting with each other for that first time. Sure, I know I’m just one man’s opinion—and the guy is typically expected to ask the majority of questions—but getting to know him better and feeling comfortable is what you’re going for, so here are some sample things to get yourself there.

10. What do you hate most about the dating process?

This one might come across as a bit of a shocker at first, but, trust me, it’s something that is actually appreciated by a guy. That’s because, well, dating can be tough. There’s the whole deal of meeting someone, then talking to them, then feeling enough of something to take them out, and then actually meet up with that person, while sharing intimate stories about yourself. Did I leave anything else out? If a girl asks me this, it’s both playful and refreshing, so I answer with complete honesty, while giving them reassurance it’s the process of dating I dislike—and not the emotional side of it.

9. Who has been your biggest influence?

This one is pretty deep, but it gets guys to think and share something that’s personal about themselves. Rather than hear about the night’s out with our buddies watching sports and boozing—which, while funny, don’t exactly show our real side—the answer to this question may actually surprise you. Who knows? The guy may say that his grandma who he talks with every weekend is the person who has taught him the most about things—which probably would be a bit unexpected to hear.

8. Favorite movie of all-time?

Much like other questions on this list, this will tell a little bit more about a guy’s personality and taste—which is always a good thing on a first date. If he answers with a comedy, he might be a bit more sarcastic. If he goes with a drama, maybe he’s more serious. Either way, getting the guy to think about things and loosen up his brain from just the same old questions is always a positive.

7. Who are your celebrity man crushes?

You might be laughing at this one, but, in all honesty, it might just be my favorite question that a girl can ask me. That’s because it shows they have a sense of humor—and that both people are comfortable enough to talk about it. While no guy is cutting out pictures in magazines of the guys that they try to most be like, there’s no doubt a few celebs who he just thinks are the coolest, most stylish, funny, witty people in show biz—so don’t be afraid to ask him about them.

6. Do you have any pet peeves?

If you want to really find out what makes a person tick, ask them this. While the guy might appear to be cool, calm and relaxed from the second you met, as soon as you ask him this, he may completely change your opinion on him—in either a good or bad way. This is a silly question that will, hopefully, make the guy let down his guard a little bit and tell you exactly what drives him crazy. Hopefully, they aren’t any things that the girl often does.

5. What do you find most attractive?

Just remember not to make this about yourself and rephrase it to ask what he finds the most attractive about you—otherwise, it might make things a lot awkward. Instead, this is a way for him to tell you what he values most in a girl and, if he’s charming, will indirectly complement you when listing a few things in his response. You might also find out that he isn’t as shallow as you first thought—if that were the case.

4. If you had $1 million, what would you do?

Whenever I hear this question, my first reply is to talk about some of my hobbies—so, girls, if that’s what you’re looking for, ask this. It shows how good the guy’s imagination might be and some of his interests, too. If his response is to fly to Vegas with his buddies and drink, that might be a good sign that he’s not your Prince Charming. But if he talks about giving some to his family or starting a business and saving most of it, you might be a lot more interested—even if he never sees one million bucks.

3. What kind of music do you like?

An absolute no-brainer, talking about music should be a requirement when two people first meet. It will get good conversation going, show if one or both of you share the same taste in tunes, determine if one or both of you are lovers of live music and, more importantly, explain why the music you often listen to is your favorite. There are few things that people are more passionate about than music, so ask away!

2. Where are three places you would want to visit/live right now?

It seems like everyone enjoys to travel, so see what places the guy would want to either visit or move to should the opportunity present itself. This will not only tell you a bit about why he chose the places he did—there might be a cool story of him going there on vacation—but is also a good way to see if you have anything more in common.

1. What were you like as a kid?

OK, so I may have mentioned that man crush one as possibly my favorite question earlier, but this is really at the top of my list. Maybe it’s because I’m just sentimental in the things that my sisters, my friends and my family did while I was younger, so I like to brag about them and the memories we made together. Each guy is obviously different, but seeing how I’m just about the same person as I was when I was still in grade school, high school and college, it’s something that I, personally, like talking about.

Photo by Chris Hondros/Getty Images

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