top of page

6 Creative Questions to Ask on a First Date

First dates can be awkward AF, especially if it’s the first one you’ve been on since a breakup.

Lana Condor (Lara Jean) and Peter Kavinsky (Noah Centineo) on a date at the diner cafe milkshakes for Netflix movie To All the Boys I've Loved Before by Jenny Han.
Photo: To All the Boys Film
 

Going on a date after a breakup can be challenging. You’re focused on making a good impression, while secretly planning your escape if the date goes south. To alleviate the stress of a post breakup first date, here are a few creative questions to help keep the conversation flowing.


1. What is the most adventurous thing you’ve ever done?


This is a good way to get an idea of the person’s personality. A response like, I enjoy swimming with sharks, can imply that the person loves adventure, while a response like hiking through Yosemite park in California, can imply that person’s sense of adventure is a bit more lowkey and not life threatening. Remember, this is not an interview but an opportunity to get to know the person on a more personal level while still keeping it fun.


2. How would your closest friends describe you?


We all have certain friends who know us better than anyone (like where the bodies are buried!). Having your date share how their closest friends portray them gives you insight to the type of person they are. It also opens the conversation to discuss your date’s circle of friends and will more than likely lead to a conversation regarding your circle of friends.


3. If you could have any person be our waiter, dead or alive who would it be?