50 Questions To Kill The Awkward Silence On Your First Date (According To A Woman)

A great first date feels effortless – time flies, the chat flows, and you don’t want it to end. A bad one feels like a hostage negotiation with a drinks menu. The make-or-break factor? How you talk. Not just what you say.

Here’s what most guys screw up: they confuse oversharing for vulnerability and treat the date like their personal TED Talk. They overshare, ramble, and unload their life story on the person across the table like an unpaid therapist. But that’s not vulnerability… it’s self-indulgence. People don’t connect with you because you’re open, they connect because you seemingly give a damn about them.

The number one complaint women have about first dates is that men don’t ask enough questions. If you want to get this right, shift the focus.

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Be Interested, Not Interesting

Here’s the truth: the most interesting person in the room isn’t the one who talks the most – it’s the one who makes everyone else feel interesting.

People love talking about themselves; it gives them a dopamine hit. Chris Williamson calls this “reverse charisma” – meaning you don’t need to be interesting to be liked. You just need to make them feel interesting.

Stop worrying about impressing your date with what you’re going to say next, and ask better questions. When you’re genuinely curious, the conversation takes care of itself. The spark happens because your date feels seen, heard, and like you actually care.

Even if the connection isn’t life-changing, you’ve both shown up and locked in for at least 45 minutes, so you may as well have some fun with the chat.

The standard “What do you do?” and “Where are you from?” are dead on arrival. Switch what for why, and they improve slightly. Though if you truly want to level up the banter and get to know her in a fun, memorable, and real way – here’s a cheat sheet of 50 questions to get you started. 

Warm-Up Round

1. What’s the dumbest thing you’ve ever Googled?
2. If I handed you $100 right now, what’s the most ridiculous thing you’d buy?
3. What’s the first photo in your camera roll? (No cheating.)
4. Which movie did you see way too young and are still traumatised by?
5. What was your first email address? (Bonus points for Hotmail cringe.)
6. What’s your most regrettable fashion phase? Did you rock a Von Dutch hat? Be honest.
7. Who topped your Spotify Wrapped, and who were you hoping it was?
8. What’s a discontinued snack you’d bring back immediately?
9. What’s the weirdest food combo you swear by?
10. If your life had a theme song right now, what would it be?

Personality Wildcards

11. What day of the week would you be?
12. What’s your personality curveball – something people would never guess about you?
13. Which reality TV show would you crush?
14. What’s the best prank you’ve ever pulled (or fallen for)?
15. F**k/Marry/Kill: Being hot, cool, or funny.
16. What’s the weirdest thing you’ve ever eaten on a dare?
17. If you could teleport anywhere for 24 hours, where would you go?
18. What’s a hobby you’ve always wanted to try but never have?
19. What’s a goal you’ll probably never accomplish but love to think about anyway?
20. If you had to combine three movies into one ridiculous masterpiece, which would they be?

Dig Into The Good Stories

21. What’s the most chaotic thing that’s happened on a holiday?
22. What was your first concert, and how do you feel about it now?
23. Who was your first celebrity crush?
24. Which song lyrics did you completely butcher for years?
25. What’s something you’ve never told your parents?
26. What’s the most random job you’ve ever had?
27. If aliens landed tomorrow, what’s the first thing you’d show them?
28. What’s the dumbest thing you’ve spent way too much money on?
29. When was the last time you disappointed your parents, and how?
30. If you could relive any year of your life, which would it be and why?

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Hypotheticals To Spark Fun (Or Chaos)

31. If you could trade lives with anyone for a day, who would it be?
32. Which movie scene do you wish you could live out in real life?
33. If you could only eat one cuisine forever, what would it be?
34. What would be your “special skill” if you were on a reality show?
35. If you could only watch one TV show on repeat for a year, what would it be?
36. If you had to live in a book or movie universe, which one would you choose?
37. Which TV or movie villain do you secretly support?
38. What’s your go-to karaoke song? 
39. What would you name your autobiography?
40. If you were famous, what would it be for?

Deep Cuts

41. What’s a book or movie that changed the way you think about life?
42. What’s the best compliment you’ve ever received?
43. When do you feel most like yourself?
44. What’s one habit you’d love to break?
45. What piece of advice would you tell 18-year-old you? 
46. What’s something small that always makes your day better?
47. What’s your non-negotiable in life?
48. What’s the most meaningful thing someone’s ever done for you?
49. Which decision did you make that completely changed your life for the better?
50. How would you like to be remembered?

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The Golden Rule

Great questions create stories. Even better questions create a connection. When in doubt, shut up and listen. Taking a genuine interest will take you much further than trying to appear interesting ever will.

While you’re here, check out some other cracking guides from evidence-based dating coach and Tinder ambassador Sera Bozza:

• How To Take A Good Dick Pic: A Complete Guide
• 10 Crucial Tips For Dating An Older Woman
• How To Nail Your Dating App Openers (According To A Woman)
• Casual Sex Etiquette 101: What Women Want You To Know
• Become A Sex God With These Simple Workouts
• 10 Things Women Look For In Your Apartment