50 Best Questions to Ask a Guy When You’re Tired of Small Talk

You’re sitting across from him at that cozy coffee shop, latte art wilting as the conversation circles back to the weather for the third time.

You laugh politely, but inside you’re screaming: ”There has to be more to this.”

We’ve all been there—the purgatory of first-date chitchat.

As someone who’s spent years guiding clients through the maze of modern dating (including a marketing exec who once texted me from a bathroom stall mid-date: ”HELP, we’re debating almond milk vs. oat milk again”), I know the key isn’t just finding “good” questions. It’s about creating doorways, not interrogations.

Let’s build those doorways together.

Save this article for later—Pin it to Pinterest and come back when you need it! 📌

---

I. Questions That Reveal Core Values (Without Sounding Like a Job Interview)

“What are your dealbreakers?” feels about as romantic as a tax audit. Try these instead:

1. ”What’s something you’ve said ‘no’ to recently that felt really powerful?” (Hi, boundaries!)
2. ”If your best friend had to describe your ‘life code’—the rules you live by—what would they say?”
3. ”When was the last time you changed your mind about something important?”
4. ”What’s a cause or belief you’d defend even if everyone else rolled their eyes?”
5. ”If you had to delete all social media except one app, which would you keep—and why?”

Why it works: A client’s brother bonded with his now-wife over question #3 when he admitted he’d switched from mocking meditation apps to using one daily after a panic attack. It wasn’t just vulnerability—it showed growth.

---

II. Emotional Intelligence Detectors

These aren’t therapy sessions, but you deserve to know if he’s fluent in feelings:
6. ”What’s a lesson about relationships you had to learn the hard way?”
7. ”When you’re overwhelmed, do you tend to talk it out, take space, or… hide in the bathroom scrolling memes?” (Light humor disarms!)
8. ”What’s a movie scene that always makes you cry—and why?”
9. ”What’s something you wish you’d handled differently in a past conflict?”
10. ”How do you usually notice when someone close to you is upset?”

Real Talk: A woman I coached once asked #8 on a park bench date. When he described sobbing at Coco’s “Remember Me” because he’d lost his abuela, it bypassed surface-level sharing entirely.

Pro Tip: Notice if his answers focus only on actions (“I buy flowers”) vs. emotional awareness (“I ask if they need solutions or just listening”). The latter? Green flag.

---

III. Questions That Uncover Life’s Texture

Forget “What do you do?” Dig into the how:
11. ”What’s a mundane part of your day you secretly love?” (My personal favorite: a guy once raved about his 6 AM walks to buy fresh bagels because it reminded him of childhood Sundays.)
12. ”What’s your ‘weird flex’—something niche you’re oddly proud of?” (Think: mastering Dad’s BBQ sauce recipe, not Bitcoin gains.)
13. ”When you’re homesick, what’s the thing you crave?”
14. ”What’s a smell that instantly transports you somewhere?”
15. ”What’s your most comforting ‘low-brow’ pleasure?” (Mine: rewatching The Office while eating cereal for dinner.)

Note: During a session last fall, a client realized her Tinder date’s answer to #13—”my sister’s terrible pumpkin bread”—revealed more about his family bond than any “Do you want kids?” question ever could.

Try This: Pair these with observations: ”You mentioned hiking—is that your ‘reset button’ or more about adventure?” Contextual follow-ups prevent it feeling like a quiz.

---

IV. Building Shared Meaning (A.K.A. Future-Testing Without the Pressure)

16. ”What’s a tradition you want to keep from your childhood—or one you want to invent?”
17. ”If we had one totally unproductive day together, what would we do?” (Bonus points if he describes something nostalgic like arcade games instead of Instagram-worthy adventures.)
18. ”What’s something you’ve always wanted to learn but haven’t yet?”
19. ”What’s your ideal Sunday in 5 years?” (Subtly reveals priorities: family brunch? Mountain biking? Lounging with pets?)
20. ”What’s a skill you think everyone should learn before 30?”

Story Time: Years ago, on a disastrous bowling date where I kept throwing gutter balls, I asked #18. His answer—”Sign language, so I could talk to my deaf cousin”—shifted the vibe from awkward to authentic instantly.

Caution: If he panics at #19, reframe: ”No wrong answers! Mine involves pancakes and zero alarms.” Soften future-focused questions with humor.

---

V. For the “Fun” That Actually Matters

Ditch “What’s your favorite color?” for:
21. ”What’s the worst advice you’ve ever given someone?” (Reveals self-awareness!)
22. ”What’s a hill you’d die on that’s completely trivial?” (Mine: Pineapple definitely belongs on pizza if you add chili flakes.)
23. ”What’s a text you sent recently that made you laugh out loud?”
24. ”What’s the most ridiculous bet you’ve ever made?”
25. ”What’s your go-to ‘we’re stuck in an elevator’ fun fact about yourself?”

Protip: When my college roommate asked #23 on a Hinge date, he showed her a thread where his mom accidentally texted ”DON’T FORGET CONDOMS” instead of ”CONDIMENTS” before his BBQ. It broke the ice and showcased his family dynamic.

Timing Matters: Save these for when conversation naturally lulls—like waiting for dessert. Forced whimsy feels cringey; organic silliness builds connection.

---

VI. When You’re Ready to Go Deeper (But Not Therapy-Level)

26. ”What’s a compliment you received that stuck with you?”
27. ”What’s something people often misunderstand about you?”
28. ”When do you feel most truly yourself?”
29. ”What’s a fear you’ve outgrown?”
30. ”What’s a moment you wish someone had witnessed?”

Client Case: A client asked #30 during a beach walk. His answer—”When I fixed my niece’s bike after she cried thinking it was broken”—showed his nurturing side better than any “Do you like kids?” question.

Safety First: Match vulnerability levels. If he shares something tender, reciprocate with equal openness—don’t leave him emotionally exposed.

---

VII. For the Culturally Curious

31. ”What’s a book/movie that changed how you see the world?”
32. ”What’s a cultural tradition you find fascinating that isn’t yours?”
33. ”What’s an underrated podcast episode you wish everyone heard?”
34. ”If you could have dinner with any fictional character, who would it be?”
35. ”What’s a piece of art (song/painting/etc.) that guts you every time?”

Pro Insight: A client bonded with her partner over #35—turns out they both get chills listening to the same obscure jazz cover. Shared aesthetic sensibilities matter!

Avoid This: Don’t fact-check his answers (”Actually, that author said…”). Curiosity > correctness.

---

VIII. When You Need to Lighten the Mood

36. ”What’s your most irrational pet peeve?”
37. ”What’s the strangest thing you’ve ever Googled?”
38. ”What’s a ‘guilty pleasure’ you don’t feel guilty about?”
39. ”What’s the worst fashion trend you’ve ever rocked?”
40. ”What’s your zombie apocalypse survival plan?”

True Story: During a tense museum date, I asked #40. His elaborate scheme involving Costco and kayaks had us laughing so hard we got shushed by security. Tension diffused.

Remember: Playful questions work best when you’re both relaxed. If he’s shy, lead with your own silly answer first.

---

IX. For the Practical Realists

41. ”What’s a household chore you secretly enjoy?”
42. ”What’s your ‘I’m adulting!’ life hack?” (Mine: freezing single lasagna portions for sad Sundays.)
43. ”What’s your relationship with your phone like?”
44. ”What’s a small luxury you’ll never give up?”
45. ”What’s your ‘emergency meal’ when cooking feels impossible?”

Why It Matters: A nurse client avoided dating a guy after his answer to #45 was ”I DoorDash daily”—lifestyle incompatibility red flag!

Frame It Right: These aren’t roommate interviews. Keep tone light: ”I’m obsessed with organizational TikTok—what’s your weird life hack?”

---

X. The Closer: Questions That Spark Future Conversations

46. ”What’s something you’ve been meaning to try but keep putting off?”
47. ”What’s a question you wish people asked you more?”
48. ”What’s a skill you’d love to teach someone?”
49. ”What’s a place you’ve been that surprised you?”
50. ”What’s something you’re currently unlearning?”

Golden Rule: End with an invitation: ”I’d love to hear more about that hike you mentioned next time.” Forward momentum > perfection.

---

Final Words from The Darling Code

Next time you’re trapped in small-talk hell, pick just one question from this list that feels authentic to you today. Maybe start with #11 while waiting for your drinks, or tuck #28 into a lazy Sunday walk.

Remember: Great connections aren’t built by rapid-fire questioning, but by attuned listening. Notice how he responds to #14 vs. #32. Does he lean in when discussing values or light up sharing childhood stories? Those clues matter more than any “right” answer.

This isn’t about “screening” him—it’s about discovering shared humanity. Because at its core, great conversation isn’t about impressing. It’s about two people saying: ”Oh, you too?”

With heart,
The Darling Code

PS: Save this to your Pinterest “Dating Advice” board, then text your group chat: “Asking [insert question here] on my date tonight—send moral support!” Progress over perfection, always.

Got value from this article? Pin it to Pinterest for easy reference and help others discover it! 🌟