5 No-Fail Questions for a First Date

5 No-Fail Questions for a First Date

By Thao Nguyen

First dates are a beast. Not a cool beast, like a dragon, but an uncomfortable beast, like if a donkey and a dragon had a baby.

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There’s pressure to present the best version of yourself without seeming like you’re trying too hard, pressure to be engaging and interesting, but not come off facetious, and in today’s social media age, the added risk of accidentally revealing everything you found out about your date in your online investigation of them. It’s basically an interview with romantic undertones, making it much more susceptible to awkwardness and mishaps.

Of course, a major factor in whether or not a first date goes well is quality of conversation. There’s only so much excruciating small talk a person can go through and so many awkward silences a person can handle. So I’ve compiled a list of questions and conversation starters that will, hopefully, keep things interesting on that first date.

  1. Do you have any nicknames?
    This will give you insight into their relationships with their friends and family, and give them a chance to share whatever story is linked to their nickname. Most likely, it’ll be a good or funny story, which will lead to laughs and overall happy feelings.

  2. What’s the worst you’ve ever messed up at work?
    It never hurts to be a little self-deprecating. Asking this question allows you to gauge how your date deals with pressure, how much pride they have, and leaves the door open for you to share your story as well. A little humility is an attractive trait in everyone!

  3. What is the best gift you’ve ever received?
    Again, a question like this provides insight into what your date appreciates and what the other people in their life do to make them happy. Depending on their answer, you can also figure out if you have common interests or a similar love language.

  4. What is your favorite thing about yourself?
    It’s hard to know what comes off confident and what comes off pompous when you’re just starting to talk to someone. This question allows your date to talk themselves up a little bit, without them feeling like they’re being vain or conceited.

  5. What is your go-to karaoke song?
    I love this question. It’s fun and sets up an opportunity for a second date! What’s not to love?

These questions have been really useful for me on dates. Some of them were questions I came up with, and some were asked of me. They really kept the conversation flowing and made me learn things I probably wouldn’t have learned until several dates in. At the end of the day, just remember that conversations are 50/50. It’s not all on you to keep things interesting, but it doesn’t hurt to be prepared!

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