First Date Questions

I once went out on a date with a friend’s co-worker. It was a little awkward to begin with, because we’d only met once and chatted very briefly. But as we sat across the table from one another, sipping our smoothies, things took a turn for the more uncomfortable. As he peppered me with questions, I suddenly felt like I was at a job interview:

  • Do you like your job?
  • Will you quit your job when you have children?
  • How many children would like to have?

Yikes. The questions came in rapid succession, and I found myself trying to sidestep talking about my most personal hopes and dreams with a guy who was essentially a stranger. Now, I know some of you are probably thinking, You have to give the guy props for being direct. Yes, I definitely picked up on the fact that he was looking for a wife. And I appreciated his intentionality. It just wasn’t first-date appropriate. And it led to me to turn down a second date.

Striking a balance between engaging in mindless small talk, on one hand, and pouring out your heart and soul, on the other, can be a challenge on a first date. We’ve all heard (or possibly experienced) the horror stories of the date who talks about all her past relationships, the date who over-shares about the addiction he’s recovering from, or, like I experienced, the “interview date.” But on the flip side, a night of mind-numbing small talk and awkward silences is no fun and doesn’t help you assess if there’s potential for a second date.

So what should you discuss on a first date? What are some first-date questions that can help you know if there should be a second? I’m going to throw a few out there to get started, and then you can add your suggestions:

  • Where did you grow up?
  • Tell me about your family.
  • When you have a day off, what’s your favorite thing to do?
  • Have you read any good books or seen any good movies recently?
  • Where was the best place you ever traveled?

Any one of these questions could lead to hours of spin-off conversations that don’t go too deep. To maximize conversation, listen well and ask follow-up questions. This technique will help you avoid awkward silences while discovering little gems of information about your date. If the date goes well, there will be other dates to ask the intentional questions. Once, when I was going on a first date (with my now-husband), my dad sent me this advice by text: “Have fun and be cool (You are!).” Along with the smiley face emoji, it was the perfect advice. I think the best first-date questions fall in the “have fun” category.

Now it’s your turn: What are some good first-date questions?

SUZANNE HADLEY GOSSELIN

Published by Intentional Faith

Devoted to a Faith that Thinks

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