5 Intriguing Questions To Ask On A Third Date

Everyone wants to make a good impression when they are courting someone new, and our list of 5 intriguing questions to ask on a third date can help. These are a good fallback once you've exhausted all those easy first date conversation starters. These intriguing questions can not only help avoid those awkward silences, they can help you learn more about one another, on the third date and beyond.

  1. What is the farthest from home you have ever gone on an impromptu road trip? The answer will tell you a lot about how adventurous (or even dangerously impulsive) your new friend can be.
  2. Who would you be portrayed by if they made a movie about your life? Not only does this question open a fun conversation about your own celebrity look-alikes, it segues nicely into discussion of your favorite actors and films.
  3. What is the strangest job you ever had? Everyone has had at least one oddball job on their way to their current career, and this question is one of those intriguing questions that can unlock a funny story or two.
  4. If you had to live in the world of a movie or TV show for one month, which would you pick? Not only can you learn more about whether you and your date have compatible tastes in entertainment, thus potentially saving you from the pain of sitting through a season of Dancing with the Stars, you can potentially learn a lot about what they see as their ideal life.
  5. What's the strangest item in your purse (or wallet) right now? That vintage miniature troll doll in your date's handbag might have an intriguing story behind it.



What Others Are Reading Right Now.

  • Speakeasy

    Acting, comedy and strong spirits converge in Speakeasy. When host Paul F. Tompkins interviews entertainers—Key and Peele, Alison Brie, Rob Delaney, Zach Galifianakis—about all sor …

  • 10 Things Women Expect Men to Know How To Do

    To make ladies swoon or at least not cringe, you’d better be able to handle the following…

  • Eats

    We all love fine food—and the people who make it! Eats introduces you to those folks, taking you into the kitchens of all kinds of culinary luminaries. From BBQ to vegan, eco-frien …