01 October 2024

First Date Cheat Sheet: 15 Conversation Starters That Always Work

Megan

15 Killer First-Date Questions (and How to Nail the Follow-Up)

Let’s be honest: first dates can feel like job interviews with cocktails. But the right questions can turn awkward small talk into a night of laughter, connection, and maybe even a second date. Here are 15 creative, fun, and revealing questions that will keep the conversation flowing—plus the follow-ups and pro tips to avoid crashing and burning.

1. If you could have dinner with any historical figure, who would it be and why?

Why it works: Shows their interests and values. Time-travel talk always wins.
Follow-up: “What’s the first question you’d ask them?”
Pro tip: If they say “Hitler,” maybe skip date #2.

2. What’s the most adventurous thing you’ve ever done?

Why it works: Reveals their wild side (or lack thereof).
Follow-up: “Is there an adventure you’re dying to try?”
Pro tip: If expired coupons count as adventure, adjust expectations.

3. If you could instantly become an expert in one thing, what would it be?

Why it works: Highlights passions and aspirations.
Follow-up: “How would you use that expertise?”
Pro tip: “Expert at dating you” is creepy. Don’t.

4. What’s your go-to karaoke song?

Why it works: Fun, lighthearted, and maybe embarrassing in the best way.
Follow-up: “Want to do a duet sometime?”
Pro tip: If they hate karaoke, suggest a duet of silence.

5. If you could trade lives with anyone for a day, who would it be?

Why it works: Shows who they admire and their dream life.
Follow-up: “What’s the first thing you’d do in their shoes?”
Pro tip: “You, so I can understand your beauty” = cringe overload.

6. What’s the worst date you’ve ever been on?

Why it works: Funny stories, plus you’ll learn their deal-breakers.
Follow-up: “Want to top that disaster with a better one tonight?”
Pro tip: If they describe your current date… ask for the check.

7. If you could only eat one cuisine forever, what would it be?

Why it works: Food always sparks good convo.
Follow-up: “What’s your favorite dish from that cuisine?”
Pro tip: If they trash the restaurant you’re in, change venues.

8. What’s your most unpopular opinion?

Why it works: Reveals quirks and possible red flags.
Follow-up: “How did you come to that conclusion?”
Pro tip: If it’s “hygiene is overrated,” skip the kiss.

9. If you could instantly learn any language, which would it be and why?

Why it works: Shows worldview and travel dreams.
Follow-up: “Where would you go to practice it?”
Pro tip: “The language of love” is cheesy. “Klingon” is… bold.

10. What’s the best piece of advice you’ve ever received?

Why it works: Reveals values and wisdom.
Follow-up: “How has that advice impacted your life?”
Pro tip: If it’s “never go on blind dates”… awkward.

11. If you could have any superpower, what would it be and how would you use it?

Why it works: Imaginative and fun.
Follow-up: “Would you be a hero or a villain?”
Pro tip: “The power to make you love me” = creepy.

12. What’s the most embarrassing thing you’d admit on a first date?

Why it works: Builds intimacy with vulnerability.
Follow-up: “Want to hear mine?”
Pro tip: Keep it light—save the heavy stuff for date three.

13. If you could wake up tomorrow with one new ability, what would it be?

Why it works: Shows what they value most.
Follow-up: “How would that change your life?”
Pro tip: “Reading minds” just screams insecurity.

14. What’s the most interesting place you’ve traveled?

Why it works: Travel stories reveal adventure and culture.
Follow-up: “What’s the top spot on your bucket list?”
Pro tip: If they’ve never left town, suggest a post-dinner walk.

15. If you could be in any movie or TV show, who would you play?

Why it works: Reveals their taste and self-image.
Follow-up: “What’s your favorite scene from it?”
Pro tip: If their character dies in 5 minutes, check their optimism levels.

The Art of the Follow-Up

  • Ask Why: “That’s interesting, what made you choose that?”

  • Share Your Take: “I’d probably pick… because…”

  • Go Deeper: “How did that experience shape you?”

  • Make It Playful: “Okay, but what if [ridiculous scenario]?”

  • Connect the Dots: “That reminds me of what you said earlier…”

Red Flags 🚩

  • Only talk about themselves

  • Rude to the waiter

  • Phone > you

  • All exes are “crazy”

  • Orders for you without asking

Green Flags ✅

  • Ask follow-up questions

  • Laugh with you (and at your jokes)

  • Conversation flows naturally

  • Remember details you shared

  • You lose track of time

Ending on a High Note

  • The Future Tease: “I’d love to hear more about [topic] sometime.”

  • The Callback: Reference something funny from earlier.

  • The Honest Approach: “I had a great time. Want to do this again?”

  • The Cliffhanger: “I’ve got a great story, but I’ll save it for next time.”

  • The Classic: “This was fun. Coffee next week?”

Level Up Your Dating Game with Bikini Sports

Want more ways to crush first dates? Check out our Love in the Fast Lane series on the Bikini Sports website. Our dating pros break down attraction, connection, and confidence—so you’ll never run out of things to say (or ways to seal the deal).

Remember: confidence is key, humor is your wingman, and genuine interest is your secret weapon. So go forth and charm away, you smooth conversationalist.