Dating conversation starters amazing, want that

33 Online Messages Guaranteed to Jump-start the Conversation


You’ve heard of twenty questions? Who hasn’t? While the last thing you want to do is assault your prospective date with inane, boring questions, you gotta get to know them somehow, right? Below are a few colorful suggestions for possible conversation starters. Hopefully with a few of these puppies peppered into your online communication, you’ll gain some intel into just who this person is, outside of their attractive profile photo.

  1. Beatles or Elvis?
  2. Would you rather watch sports, reality TV or ”The Simpsons”?
  3. Which piece do you pick in Monopoly? (I mean, if you both insist on being the racecar, there will some confusion at Free Parking …)
  4. What was your favorite toy? Either as a child or now…
  5. How do you feel about pirates?
  6. What do you hate about playdates?
  7. What makes you happy when you’re in traffic?
  8. Team Edward, Team Jacob or the Chicago Cubs? 
  9. Would you ask (insert fabulous famous person) for an autograph?
  10. Which Peanuts character do you most identify with?
  11. Ketchup on eggs? Awesome or gross?
  12. Europe or the Caribbean?
  13. What song do you turn down when another car pulls up to the light?
  14. What is the strangest thing your kid ever ate?
  15. The conspiracy theory I BELIEVE is…
  16. Juice boxes or juice pouches?
  17. Kickball or four square?
  18. How do you feel about the threat of a global thermonuclear meltdown? (Haha. Don’t ask that. Unless you’re dating Hillary Clinton.)
  19. Tupac: Dead or alive?
  20. What is the best thing about your mom / dad?
  21. What is the best thing about BEING a mom / dad?
  22. What is your favorite potato product? (Tater Tots are keepers!)
  23. Should Pete Rose be in the Hall of Fame? (Follow-up: Do you know who Pete Rose is?)
  24. Is your kid more of a teeter-totter-girl or a slide-man? Obviously, tailor the gender appropriately.
  25. If you weren’t a parent, what kind of car would you drive? 
  26. “Law & Order” or “CSI”?
  27. I was most disappointed when I didn’t get _______________for my birthday.
  28. Bruce Springsteen: Profit-sell-out or prophet-genius?
  29. Which Disney film would you like to push off a very tall cliff?
  30. Did you teach the kid to tie his shoes or figure, F*!# it, here’s some Velcro?
  31. Do you actually like the parents of your son’s / daughter’s playdates or do you just fake it to keep the peace?
  32. Which celebrity do people say you most resemble… …that insults you?
  33. What makes single moms or single dads unique?

One thing to remember: how your potential coffee dates answer the questions is often just as important as the answer itself. For example, if you ask “How do you feel about pirates?” and they ask “How is that relevant?” – well, you’ll know they probably aren’t 10s in the humor category. You handed them gold for goodness sake. Or if the response to “Which Disney film would you like to push off a very tall cliff?” is “Oh, I love them ALL,” well, you’ll know they’re liars. Happy bantering.

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