70+ First-Date Questions to Keep the Conversation Moving

Every first date needs a silly question or two. The following can help you each relax and lighten the mood. Best paired with a coy smile or a cheeky little wink.

• What's your best dad joke?
• What's your cheesiest pickup line? I want to see if it actually works.
• What's your worst first-date story?
• On a scale of 1 to nightmare, how embarrassing was your first kiss?
• What was the weirdest thing your younger self did?
• What's the most embarrassing thing you've done on a date?
• What nicknames do your friends and family call you?
• What's the most outrageous lie you told as a kid?
• If you had to go on a reality dating show, which would it be and why?
• What show or movie do you quote the most?
• What are your go-to memes?