8 Questions You Should Ask on a First Date

8 Questions to Ask on a First Date


There’s only so much you can learn about a person by asking what their favorite color is and what kind of food they like to eat. Here’s some conversation starters and questions to ask on a first date that won’t send your date running for the hills, and will help you decide if a second date is going to be worth your time.

What’s your guilty pleasure?

Is their guilty pleasure a deal breaker? Or is it something you would be interested in trying?

What do you like to do in your free time?

Are they the type of person who loves to sit at home and play video games all day? Or are they helping at homeless shelters, making music, or writing short stories?

What is your dream job?

This could give you a good idea what some of their goals and aspirations are. Or it may give you a window into a different side of them - maybe they have a degree in business, but they’ve always wanted to be a pilot.

What’s the best thing that happened to you this week?

It’s a casual question that not only shows you’re interested in their lives, but also gives them a chance to brag about how their sister just had a baby, or their boss finally recognized all the hard work they’ve been doing for the past month. It can help ease the tension and awkwardness of the first date. If you’re lucky, they might ask you the same question and you’ll get a chance to brag about the promotion you just got or the $20 you found laying on the ground outside the grocery store.


What’s something you’re always down to do?

This will be the go-to when you guys are bored and sitting on the couch wondering what to do with your day. Most likely, this will turn into something that becomes “your thing” that you guys do together as a couple. Make sure it’s something you wouldn’t mind doing regularly.

What’s your favorite thing to do where you live?

This is another question that kind of gives you an idea of what they do in their free time. Have they gotten out and explored the town? Maybe there’s an activity they’d love to do with you, or a favorite restaurant you could visit together. Not only does it tell you about the person, but it gives you ideas for potential future dates.

Which parent is your biggest role model?

Who are they closer to, Mom or Dad? This opens a chance for you to hear a little about their family and how they view the accomplishments of others.

What’s your biggest pet peeve?

Hopefully they don’t answer with something you’re guilty of doing all the time! But you can also figure out if they are the kind of person who is annoyed by little insignificant things or if it takes a lot to get them aggravated. It’s an opportunity to see if you’re signing up to be with someone who can’t stand your little quirks.

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