10 Questions To Ask On A First Date

November 20, 2015 by ashley kaylor
shefinds | |

You’re on a first date. At this point, you’ve covered the standard first-date questions: Where did you grow up? What do you do for a living? What do you do for fun? Blah blah. It’s great to get those questions answered and out of the way, but it’s time to shake things up! Here are 10 playful questions to have up your sleeve should your awkward silences need filling.

1. What’s on your bucket list?

This question will not only make your date think outside the box, but will also open up conversation than can lead any direction! Get creative!

2. Do you have any nicknames?

Make sure you’re only asking this question if you’re comfortable with yours, otherwise you’re setting yourself up for high school flashbacks…and we don’t want that!

3.  Are you a traveler? If so, where have you been?

Through this question, you’ll learn whether they are adventurous or more of a homebody. Most importantly, you will have a better idea about how compatible the two of you could be.

4. What do you find attractive?

You aren’t asking if they find you attractive – lets not get carried away just yet. BUT if they do say “you,” you really can’t complain! More importantly, you will learn what qualities they value most.

5. What’s your favorite curse word?

Is this question really beneficial? No, probably not, but if you’re like me a little sass can’t hurt.

6. What makes you nervous?

Heights? Public speaking? Relationships? This question will let your date show their vulnerable side, and admit to something they’re not entirely comfortable with. To ease any tension, put your two cents in first!

7. What’s something you’re bad at?

This isn’t meant to prompt a confession of your date’s failures. The best way to approach it is by offering an example of your own. It’s a way of letting your guard down and relating. Vulnerability can be extremely attractive.

8. What’s your biggest pet peeve?

Cross your fingers you haven’t done any of them!

9. What was the worst first date you’ve ever been on?

Oh C’mon! Why not? Everyone has at least one story! Live a little.

10. Are you a morning person or a night person?

If he’s a morning person… well, then you may have just opened up another flirty conversation. Get ready!




About the author: Ashley Kaylor is a professional matchmaker in New York City. Stay Connected On FB: Matchmaker of Love & Lifestyle or Follow her on Twitter @ashley_kaylor!

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