— Very Important Questions

10 unexpectedly fun questions to ask on a first date

First dates can be exciting and awesome, but they can also be nerve-wracking, awkward, and pretty flippin’ weird. If you’re anything like me, the conversation will invariably turn to boring work stories and how much you’re addicted to guacamole. And while that makes for a fine two minutes of chit-chat, more substantial convesation is obviously necessary to get to know someone.

So why not open the floodgates with some compelling questions? Forget the standard “So, what do you do?” and spark some in-depth discussions that get a little personal in all the right ways. Consider popping a few of these questions on your next first date and see where they lead the conversation. If nothing else, you’re bound to get some interesting answers.

What’s your most vivid childhood memory?

Maybe it’s about being with their pet dog in the backyard or the smell of their grandmother’s house. Childhood memories are funny things: They reveal a lot about the way you think about the world, and the way you looked at it from a young age. It’s a great way to learn a little bit more about their background and spark a discussion about the way you both grew up.

Who in your family are you closest too?

You want to know where someone came from, but it can be a delicate subject. (Maybe their relationship with one of their parents or siblings isn’t great.) This is a nice way to leave it open-ended, and let your date chat about their family in terms that are as specific or as general as they want. It shows interest without being intrusive.

Were you popular in high school?

Oh, high school. As long as you’ve got a couple years to cushion you from it, it can be a time that’s rich with funny stories and little observations. The way that someone saw themselves in high school when they were figuring it all out can say a lot about who they are. Were they super into sports? Did they go to prom? Did they sneak out after curfew? Earn straight As? What do they wish they could have done differently, if anything? What were their friends like? You don’t have to rapid fire interrogate someone, of course, but it can lead to a conversation about their past that’s meaningful but still light.

What’s something you’re bad at?

This isn’t meant to prompt a confession of your date’s failures. The best way to approach it is as a light-hearted thing by offering an example of your own. Maybe: “I’m really bad at cooking. I managed to burn cereal one time. What about you, what do you wish you were better at?” Or, “True fact, I didn’t learn how to tie my shoes until I was in high school.” It’s a way of letting your guard down and laughing at yourself, a very attractive quality, and an invitation for your date to do the same.

What’s something you’ve been really proud of lately?

Maybe it’s hitting a time goal on a run or learning how to make pesto or finally getting the hang of something at work. It opens up room to hear about what they value without making your date feel like they’re bragging. And you can share, too!

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