Let’s be honest, small talk is the worst. And first dates can be a horrific black hole of small talk. You’re feeling each other out, trying to figure out if you like this person enough to go on a second date. But does exchanging information about what you do or your hobbies really let you get to know someone?
In the interest of skipping past the boring part of dates, here are 30 questions to ask. They may feel a little awkward but you want to get past small talk and at least reach medium talk. So use some of these questions as a jumping off point to dig a little deeper. Ain’t nobody got time to be bored.
What was the first CD you ever owned?
What was your favorite Halloween costume as a kid?
What was the worst thing you’ve ever done?
If you could do any job, what would it be?
Have you ever had a close female friend?
What 4 people would you invite to a dinner party?
If you knew you couldn’t fail, what thing would you try?
When are you at your happiest?
Coolest thing you owned as a kid?
If you could go anywhere in the world, where would you go?
Have you ever been in love?
Do you have a lot of friends or do you like to keep it to a couple of good friends?
What’s the most daring thing you’ve ever done?
How old were you when you had your first kiss?
What two celebrities would you like to see cage fight each other?
How would you want to die?
If you were on Shark Tank what would your idea be?
What’s your favorite movie? What’s your favorite guilty pleasure movie? Favorite bad movie?
What TV show or movie did you watch a lot as a child?
Who is your least favorite celebrity?
What’s the weirdest thing about where you grew up?
Who’s your favorite serial killer?
Would you rather be blind or deaf?
Do you think you operate more on logic or emotion?
What is your best memory?
If you could see the future what would you want to know?
If you died tonight is there anything you’d regret not telling someone?
If you won the lottery what’s the one thing you’d want to buy?
Do you want to do a murder? (Okay maybe not that last one. If they laugh they’re probably cool but you could also freak them out. Also if they seem genuinely interested I’d run.)
So next time you’re sitting next to a stranger, trying to think of conversation starters, get straight to the good stuff. Don’t ask someone what they do, find out about what they want to do.
What’s the best question you’ve heard on a first date? Let us know in the comments below.