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5 Things to Ask On a First Date to Keep It Interesting

Here’s the scenario: you meet someone online that you think has real potential and ask them out. The date is approaching and you’re already freaking out about what you’ll talk about. You want to hold their attention and make the best impression possible.

One of the biggest pitfalls of first dates is that they sometimes have the tendency to feel like job interviews. Here are a few clever things to ask your date that will help you learn more about them while keeping the conversation interesting.

  1. If you were given a free airline ticket and accommodation, where would you most like to go?

In my experience, everyone gets excited about traveling— especially when it involves daydreaming about their ultimate fantasy destination (sidebar: if they don’t, then this question is a good litmus test!) Whether it’s a trip to the Maldives or hiking Mt. Kilimanjaro, you can learn so much about a person based on where they’ve been and where they’d like to go.

  1. What’s on your bucket list?

Similar to question #1, it’s always interesting to hear about someone’s bucket list. Learning about someone’s weird and wacky dreams (go swimming with dolphins! Travel to China! Eat an Ostrich burger!) is often very revelatory and beats asking, “So, where do you see yourself in 5 or 10 years?”

  1. What did you want to be when you grew up?

This is a great way to find out what someone was like when they were younger without coming off like a therapist (example, “So tell me about your childhood”). It’s always fun to look back at being a kid and laugh at all the things you didn’t know — for example, when I was seven years old, my dream job was “ballerina/private detective/pop star” and it totally came true! (Just kidding).

In lieu of asking “So, what do you do?” this question allows you to segue into getting your date to talk about their career. Does their current job at all line up with their dreams? This is something I’m always curious about when I’m getting to know someone new.

  1. If you could design your dream concert lineup of artists (living or dead), who would be on the marquee?

I love asking this question because it’s so much more fun than just asking them, “So, um, do you like music?” People tend to get excited when they’re talking about their favorite artists. Plus, if the other person says they’d include 2Pac and Prince, I pretty much know that we’re destined to be soulmates. On the flipside, if they say “I don’t really know” or “I’m not really into music”  it’s a good indication that we don’t have a whole lot in common.

  1. What’s the most important thing you’ve learned in the past 12 months?

Not only is this question super clever and original, but it’s also a great way to take the date to a deeper place emotionally without saying, “TELL ME ALL OF YOUR DEEP DARK SECRETS.” Whether it’s a big work victory or something they learned about relationships, most people welcome the chance to reflect — something that doesn’t usually happen when you ask generic date questions.


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