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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?

If you find that there is silence between you and your date, this question will definitely lighten up the mood and is an open ended question that can lead to a great conversation. For example, if your date says Post Malone, that could lead to a conversation on favorite songs or the meaning behind all of his tattoos. It's another good question to get to know your dates interests and also keep the conversation flowing.

4. If you were offered a million dollars to give up your favorite snack would you take the money?

If you want to laugh with your date I would suggest that you add this into a conversation at some point. You’d be surprised by the answer and what snack your date may or may not be willing to give up! It will also more than likely prompt your date to ask you the same question and will give him/her some insight to your favorite snacks.

5. Who is someone in your life that you admire?

If the date is going well you may want to start asking deeper questions and asking about someone who has inspired him/her can get pretty deep. It will give you an idea of their values and what inspires them. It will also allow you a glimpse into how they see their future while allowing you both the opportunity to share on a deeper level.

6. If you could live in one moment for the rest of your life, which moment would you choose?

I saved the best for last and a question you could use towards the end of your date; depending on how it went. Their answer to this question will exemplify a small part of who they are and what’s most important to them. For some it may be success while for others it may be something as simple as being married to someone you consider your best friend.

Whenever you're ready to get back out there and start dating again, keep in mind that this first date is an opportunity to start new. And remember, it’s never a good practice to bring up your last boyfriend. Opting to start dating again means you are open to move forward so don’t bring your old baggage.


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