Try These Failsafe First-Date Conversation Starters on Your Next Night Out

By
Hadley Mendelsohn
Hadley Mendelsohn
Hadley was the Associate Editor at MyDomaine for two and a half years before joining the House Beautiful team as the Design Editor.
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Updated on 01/10/22 08:40PM
Portrait of stylish black couple at summer street cafe.

Evgeniia Siiankovskaia/Getty Images

Do you remember the first date you ever went on? I do, and not because it was full of memorable moments that marked the beginning of a great romance. The part I remember most is running off to the bathroom to call all my friends until one of them finally picked up to tell me what in the world I should talk about next. Of course, I now understand that a date usually goes well if the chemistry is right, and my question-asking ability isn't the cure-all for an awkward match. But it would've helped to have some first-date conversation starters up my sleeve to ease the lulls.

To help you out, we came up with some ideas so you don't have to rush off to the bathroom in a panic like me. We broke these conversation starters down into three categories — initial background information questions, ice-breakers, creative and out-of-the-box prompts — and we'll also tackle how to keep the date going or gracefully put it to an end.

Read on for some fail-safe first-date conversation starters.

Start With the Basics

Even though it can be boring to ask run-of-the-mill questions, you have to start somewhere, and the basics aren't a bad place to do so. Once you know more about your date's background, you'll be able to guide the conversation to more interesting places.

Be sure to avoid asking rapid-fire questions—it may feel more like an interrogation. Instead, engage their responses with follow-up questions or offer pieces of information about yourself.

Here are some questions to consider:

  • How do you spend your days?
  • Where did you grow up? Is it different from where you live now?
  • How long have you lived here? Are you liking it?
  • What were you interested in while you were in school?
  • What's your family like? Do you have a favorite childhood memory?
  • What do you like to do for fun? Any hobbies or passions?

Break the Ice

Rather than asking what they do for a living and where they come from, you can ask little anecdotal questions that give you a glimpse into what their personality is like. Hopefully, this leads to some banter or helps you find out some overlapping interests, qualities, and preferences.

  • What are your favorite travel destinations and why?
  • Do you like movies or TV shows better?
  • Have you gone to any cool exhibits or shows recently?
  • Are you a dog or a cat person?
  • Are you an early bird or a night owl?
  • When's your birthday?
  • What do you and your friends do for fun?
  • Do you like what you do? What's next? What's your dream job?
  • What's your perfect day?

Keep Things Interesting

If small talk bores you, consider getting more creative with your questions. You could end up finding out more about them than you expected, for better or for worse. But, of course, only ask the questions you're interested in learning the answers to.

  • What are the little things that always make your day better?
  • If you could relive any day, what would it be?
  • Are you an idealist, a pessimist, or a realist?
  • If you could have dinner and drinks with any three people, dead or alive, who would they be?
  • What was your favorite cartoon as a kid?
  • Have you done anything embarrassing lately?
  • What makes you laugh?
  • What's an accomplishment you're proud of?
  • What were the weirdest quirks and habits you had as a kid?
  • What item in your bedroom do you most represent or personify?
  • What one quality do you wish you had?

Continue or Call It

Once you go over all of the background information and learn a little more about one another, you'll probably feel more comfortable (even if the date isn't a match made in heaven). But if it's going badly and you still feel really awkward or you aren't sure how to fill the silences, you could give it one more shot with an open question or subtly put things to an end. Likewise, if it's going really well, you could extend the date or end it on a positive note.

  • I'm looking for some new restaurants to try in the area for a work dinner next week. Do you have any suggestions?
  • How's the rest of your workweek looking? Do you have any fun weekend plans?
  • I just finished my favorite TV show and need something new to watch. Have you watched anything good lately that you'd recommend?
  • I have a pretty long day tomorrow and need to be up early. Let's grab the check?
  • I didn't realize it was getting so late! I promised my roommate we'd grab dessert, so I should be heading back soon.
  • Should we get another round, or are you ready to split the bill?
  • There's a really cool bar around the corner. Want to switch scenes and check it out?

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