21 First Date Questions That Are Better Than Small Talk
Stop asking 'What do you do?'. Use these 21 questions to vet for chemistry, compatibility, and red flags without making it feel like an interview.
First dates are a delicate dance. You want to get to know them, but you don't want to grill them. You want to be deep, but not too deep too soon.
The standard "interview script" (Where are you from? What do you do? How many siblings?) is safe, but it’s boring. It doesn't tell you who they are.
Here are 21 first date questions designed to reveal personality, values, and chemistry.
The "Vibe Check" Questions
Gauge their energy and outlook on life.
1. "What’s the best thing that happened to you this week?"
The Intel: Are they an optimist or a complainer? Do they find joy in small things (a good bagel) or big things (a promotion)?
2. "What are you looking forward to right now?"
The Intel: Shows their ambition and future orientation. A person with nothing to look forward to might be stuck in a rut.
3. "How do you usually spend your weekends?"
The Intel: Lifestyle compatibility check. If they party until 4 a.m. and you hike at 7 a.m., you need to know now.
4. "What is your favorite way to relax?"
The Intel: Introvert vs. Extrovert check. Do they recharge alone or with people?
The "Personality Reveal" Questions
Figure out what makes them tick.
5. "What was the last show you binge-watched?"
The Intel: Shared interests. Bonding over The Office or Succession is an easy win.
6. "If you could travel anywhere tomorrow, where would you go?"
The Intel: Adventure level. Are they dreaming of a resort in Mexico (relaxing) or backpacking in Peru (adventurous)?
7. "What is a skill you’ve always wanted to learn?"
The Intel: Growth mindset. Are they curious? Do they want to improve themselves?
8. "Who is the most interesting person you know?"
The Intel: Shows what they value in others. Do they admire their rich boss? Their kind grandmother? Their wild best friend?
9. "What is your biggest pet peeve?"
The Intel: Tolerance level. Is their pet peeve "rude people" (reasonable) or "loud chewing" (specific)? It’s also a fun way to bond over shared annoyances.
The "Deeper Compatibility" Questions
Subtle ways to check for values.
10. "What is the most spontaneous thing you’ve ever done?"
The Intel: Risk tolerance.
11. "What is a cause you care about?"
The Intel: Values check. Animals? Environment? Social justice?
12. "What does a 'balanced life' look like to you?"
The Intel: Work-life balance. Are they a workaholic? Do they value family time?
13. "If you won the lottery, what would you do with your time?"
The Intel: Reveals their true passions if money wasn't an object.
14. "What is the best gift you’ve ever received?"
The Intel: Love language check. Was it a thoughtful handmade item or an expensive gadget?
The "Fun & Flirty" Questions
Keep the spark alive.
15. "What is your go-to karaoke song?"
The Intel: Confidence level. Even if they don't sing, the answer tells you if they are fun.
16. "Have you ever had a supernatural experience?"
The Intel: It’s a weird question, but everyone loves telling ghost stories. It builds intimacy through fear/excitement.
17. "What is the worst pickup line you’ve ever heard?"
The Intel: Humor. It allows you to laugh at the dating game together.
18. "If we were to escape town right now, where should we drive?"
The Intel: Spontaneity and imagination. It plants the seed of a future adventure together.
The Closers
Wrap it up on a high note.
19. "What is the best advice you've ever ignored?"
The Intel: Shows a rebellious streak or a lesson learned the hard way.
20. "What are you obsessed with right now?"
The Intel: Whether it's a new band, a video game, or a type of cheese—passion is contagious.
21. "Does this place have good dessert, or should we go somewhere else?"
The Intel: The ultimate test. If they say "Let's go somewhere else," the date is going well.
Conclusion
Use these questions as a menu, not a checklist. The goal is to find one thread—travel, food, ghosts—and pull on it until you're both laughing and forgetting to check your phones.
