1. Ask him, “If you could be doing anything humanly possible right now, what would it be?” It’s always good to have a few icebreaker questions on standby. Go for original, absurd and goofy, or thought-provoking. If he says, “I’d still rather be here with you!” dump his cheesy ass.
2. Ask him where he sees himself in five years. All too often, first dates are about the “now.” What do you do for a living? Where do you live? Instead, ask him where he wants to be. Most Millennials aren’t working their dream job or even working in the field they’ll end up in for most of their life, anyway.
3. Ask anything that lets him show off. Please, just … throw him a bone. Anytime he says something that sounds like a humblebrag, follow up on it. That’s what he wants. By no means let him dominate the conversation, but, when it’s his turn to talk, if he’s giving you very clear hints about things he’s proud of, do the man a favor and ask him about it.
4. Ask, “What’s your perfect date?” Secretly, he’s dying inside for you to ask this, so he can tell you. That way, you’ve got a great second date idea, and he doesn’t have to plan it.
5. Ask for major turn-offs and pet peeves. This is a question that’s potentially frightening to ask and could score you some offensive answers. But if you both share your ultimate deal breakers off the top, it could save you some time. Some of those don’t rear their heads until it’s way too late.
6. Ask him if he’s as nervous as you are. First dates are nerve-wracking for a lot of people. Unless you’re incredibly confident or a sociopath (is there a difference?), you’re probably a little freaked out. Plus, this is 2016 … there’s a good chance this is your first time even meeting your date in person. Acknowledging that can help put both of you at ease.
7. Ask if he wants to have sex. So you know what you are in for. Being honest about this will go a long way even before the relationship starts.
8. Ask him to tell his favorite joke. This is incredibly telling. Even if he doesn’t have a favorite joke, that says a lot. Maybe it’s corny or pun-based or it’s an anti-joke, but you’ll know if you’ve got similar senses of humor. And if you have to push him to tell it because he’s embarrassed, you know it’s going to be good.
9. Ask if he wants to split the check. No, chivalry isn’t dead, but who doesn’t really want to split the check deep down? What does paying for the whole meal really show? If you’ve asked him every awkward question on this list, he’s probably earned it.