Try these 10 NEW questions to ask on a first date

10 questions to ask on a first date

We’ve all been on way too many boring first dates. It’s always the same old routine – Where are you from? … What are your hobbies? … Do you have any siblings? … yawn! Why not mix it up with some new, unique questions? Here are 10 fun new questions to ask on your next first date.



1. What was your first AIM/ICQ screen name?

Everyone had embarrassing moments at age 11, and finding out that your date’s screen name was dolphincuddles92 or britneyfan488 just makes them seem way less intimidating. It’s also fun to bond over the shared nostalgia of a simpler time.

2. What was the first album you ever owned?

Maybe you two will bond over the fact that you both still love Boys II Men or Mariah Carey.

3. What’s the most embarrassing thing you’ve ever binge-watched?

For me it’s 8 seasons of Doctor Who during one especially uneventful summer. You can learn a lot about a person from their binge-watching history.

4. Assuming you won’t be able to change anything, would you rather time-travel to the future or the past?

I like this question because you get to learn about their outlook on life. Are they a history buff who can’t pass up the opportunity to chill with Cleopatra, or they a sci-fi fan who would love to see humanity’s future?

5. Which superpower would you most want to have, and why?

Would you pick flying, x-ray vision, teleportation, controlling the weather…? The possibilities are endless.

6. Would you rather never be able to eat your favorite food ever again or have to eat it for every meal for the rest of your life?

This “would you rather” question gives you some perspective about their feelings on routine vs. spontaneity. Or maybe you’ll just find out that they really really love pepperoni pizza.

7. Would you rather have your mom read through your browser history or not be able to use the internet for a month?

It’s interesting to think about how much we rely on technology and just how human it is to Google embarrassing things.

8. What was your favorite subject in school?

Maybe you’ll find out your date is secretly a huge art history nerd, or maybe you’ll bond over your mutual dislike of chemistry lab. Either way, it’s usually fun to reminisce about your schooldays.

9. What’s the weirdest thing you’ve ever eaten?

This is usually accompanied by some interesting story about how they tried deep-fried scorpion in a Beijing night market, puffin burgers in Iceland, or squirrel jerky from their cousin’s hunting trip. It also gives you some insight about how adventurous they are.

10. Where’s the craziest place you’ve ever had sex?

Feel out the situation first. Not everyone is comfortable talking about sex on a first date, but many people – myself included – think it can be a fun and flirty topic of conversation.


Try out a few of these questions to spice up your next first date. Have a dating or romance question? Contact us! We always love hearing from you.

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