The Best Questions to ask on a First Date

We all know that there are certain topics you should avoid while on a first date. Most first dates are but a doorway to better things, like sex and, if you’re really lucky, a loving a relationship; they’re not debates or game shows.

So it’s important to avoid any topics that might lead to heated disagreement, and it’s definitely important to avoid asking any imposing, aggressive questions.

You might really love to know whether your date is closer to Ron Jeremy or Mini Me underneath the zipper, but asking him where his love needle falls on the scale from mouse to donkey isn’t the best question to ask on a first date. Likewise, all you men out there, asking your date about the biggest thing she ever fit into her mouth can be a real mood killer, unless you’re actually paying your “date” by the hour.

In short, there are some pretty bad questions you can ask. No, they’re not all sexually-driven. Asking about politics and religion and exes can also lead to embittered dialogue, the type which neither of you will forgive.

The idea on a first date is to keep things civil and interesting. You want to be inquisitive without being intrusive. Your aim should be to come across as mildly flirty without seeming too provocative and obnoxious.

Date conversation should go something like this, ideally:

Good example: Wow. Where did you get that dress? It’s stunning.

Bad example: Damn, girl; how did you fit those boobs into that dress!?

Yeah, you get the idea. So, without further ado, here are some of the best questions you can ask on a first date.

What’s your dream in life?

This question is definitely nonintrusive and it can lead to an entire night’s worth of ebb and flow, back-and-forth, naturally evolving conversation. Asking what your date really wants to do with his or her life is safe, interesting, and makes you appear as if you actually care about the answer when we all know you just want to avoid the awkwardness long enough to score.

Most dates won’t have any problem answering a question like this. The only “iffy” part about it is that the answer might be a short “I don’t know,” in which case you’ll have to interject and tell a little bit about yourself to save the date. No big deal. It’s a question worth asking, definitely.

If you could have a conversation with anyone, who would it be?

This question could act like the first and lead into good conversation, but we’re not too worried about that. This particular question stands out as one of the best because it allows you to get a read on your date.

If your date gives an answer like her grandmother or if he says something like George Washington, then there’s no need to fret. Some dates might blurt out something like Ted Bundy or the Unibomber! And while this might be scary, at least you’ll know on the first date that your follow-up phone call should be to the FBI.

What type of music do you like?

Yeah, I know: there’s certainly nothing original or thought-provoking about this question. This is about as bland and clichéd as a question gets. So why is it on the list as one of the best first date questions to ask? Well, it has to do with the type of technology we have nowadays.

Music is everywhere – on your iPods and iPhones and on your extended cable channels and everywhere in between. If the relationship is to work, you can’t in good conscience stay with a person who hates country music if it’s your favorite type of music. And we all need to know if our dates like Justin Bieber or not. If yes, sayonara. We don’t need that in our lives!

Is there anything that you just can’t say no to?

Here’s another attempt to get a read on our dates. We want to do a little bit of research here for the future. Sure, it can be a great launching pad for a conversation. It’s a gentle question that, like the first on the list, makes your date think you honestly care about the answer. But what we’re really looking for is a way to score some points in the future.

If your date absolutely can’t resist fudge brownies, then we know what to bring them before the second date. See how that works? There’s no way this can ever be a bad question. Well, on second thought, it can be bad if the answer is disconcerting.

If you’re on a date with a girl and she answers that she just can’t resist having sex with random guys, you’ll be in a tough spot come the morning.

Have you ever been in love?

This is a question with the sole purpose of showing off a little bit of your romantic side without having to use any cheesy lines that may embarrass you. When you ask this, your date automatically gets the sense that you’re the romantic type, so it’s up to them to fill in the empty space with whatever they see fit.

The answer should be a yes in most cases, which should lead to your date posing the same question to you. When this happens, you can shine by saying something like, “Well, I’m really hoping to find love.”

Oh, you’ll be in a good position for the rest of the night, to be sure.