10 First Date Questions to Ask

Cat got your tongue? First dates can be nerve-wracking. Here are a few questions to help break the ice.

1. How was your day?

Right off the bat, show an interest in your date’s life. It’s easy to launch into “date mode” and forget that your date had a full day before you met up.

2. What do you do for fun? What are you passionate about?

What someone does for a living is rarely as telling as what someone likes to do with their free time. It’s an especially great question if you suspect your date isn’t exactly thrilled with their current employment situation.

3. How do you define success?

Some people are counting down the days to retirement. Others are working hard to climb the corporate ladder. And some just want to feel good about themselves at the end of the day. “Success” looks different to everyone. Find out what it means to your date.

4. What’s your signature drink?

Related: How do you take your coffee?

This is a fun, no-pressure question that can break the ice early on. If you meet up at a bar (or coffee shop), take a mental note. It will come in handy on Date #2.

5. Who do you usually go to for advice?

Instead of launching into lists of family members and best friends, this question helps focus the conversation on people who are currently influential in your lives.

6. What’s the scariest thing you’ve ever done?

Get a good (and revealing) story out of your date. Maybe he’s jumped out of a plane. Maybe she took over the family business. Maybe he moved across the country to attend his dream school. Just be prepared to share your answer to the question, too.

7. What’s the best meal you’ve ever had?

Warning: Don’t ask this question when you’re hungry. It will make those pangs worse.

8. Where do you most feel “at home”?
Instead of asking, “Where are you from?” ask about home. “Home” and “from” aren’t always the same thing.

9. If you had to learn a new skill, what would it be?

You’re giving your date a chance to dream a little — and reveal an area they’re not confident/skilled in. Maybe your date can’t drive. Maybe she can’t play an instrument. Maybe he wishes he could cook better. (If the date goes well, maybe you’ll eventually sign up for a couples’ cooking class together.)

10. What’s on your bucket list?

Does she want to eat escargot in France? Does he want to climb Mount Everest? Maybe she wants to be published. Or he hopes to build his own cabin in the woods.

Dream out loud together. Maybe you’ll find you have some dreams in common.