You know that awkward silence? When you're scrambling for something to say? Happened to me last month at a conference. I asked about the weather. Dead end. Then I remembered my list of best questions to ask someone - switched gears and suddenly we talked for an hour. That's what I want to share today: how questions can build bridges or burn them.
Why Your Question Choice Makes or Breaks Connections
Ever notice how some people leave conversations feeling energized while others drain you? It's usually about the questions. Generic questions get generic answers. But the best questions to ask someone do three things:
- Dig beneath the surface (Instead of "How's work?" try "What surprised you at work this month?")
- Invite storytelling (People light up when sharing experiences)
- Show genuine interest (Forces you to actively listen)
I learned this the hard way. My neighbor always gave one-word answers until I asked about the photo of his vintage motorcycle. Turns out he rebuilt it after his divorce. We've been friends for years now.
Situational Question Toolkits
First Date Goldmine Questions
Dating apps made conversations transactional. Break the pattern:
| Question | Why It Works | Avoid This Instead |
|---|---|---|
| "What's something you believed as a kid that seems ridiculous now?" | Reveals humor and vulnerability | "What do you do for fun?" (Too generic) |
| "What's one rule you love breaking?" | Shows personality and values | "How many siblings do you have?" (Factual, no depth) |
| "Where would you teleport right now if you could?" | Unlocks dreams and spontaneity | "What's your favorite color?" (Seriously?) |
My worst date ever? Guy asked about my salary and exes. Don't be that person.
Pro Tip: Notice their hobbies and ask "What first got you into [hobby]?" Better than "Tell me about your hobbies."
Networking That Doesn't Feel Sleazy
Forget "What do you do?" at events. These work better:
- "What's exciting in your world right now?" (Positive framing)
- "What problem are you currently obsessed with solving?" (Shows passion)
- "Who's inspired you recently in our industry?" (Reveals influences)
I met a CEO who later hired me because I asked about her nonprofit work instead of her company revenue.
Deepening Existing Relationships
With friends or partners, push beyond routines:
| For shared history: | "What memory of us makes you smile unexpectedly?" |
| For emotional check-ins: | "What's weighing on you that nobody's asking about?" (Give space to decline answering) |
| For future dreams: | "If failure wasn't possible, what would you attempt next year?" |
The Question Formula That Never Fails
Want to create your own best questions to ask someone? Mix these elements:
- Anchor to specifics: "That story about Tokyo - what smelled strongest when you stepped off the plane?"
- Invoke imagination: "If you had to teach a class on one random skill you have, what would it be?"
- Time travel: "What would 10-year-old you think about your life today?"
Experiment framework: [Emotion] + [Specific Detail] + [Open-Ended Phrasing] Example: "Frustrating as it must've been during the project delay, what actually improved because of it?"
Landmine Questions to Avoid
Some questions backfire spectacularly:
- "Why are you still single?" (Assumes being single is wrong)
- "How much did that cost?" (Puts people on defensive)
- "Are you pregnant?" (Just... don't)
My cringe moment: Asking a vegan friend why she "gave up real food." Took weeks to repair that.
When Good Questions Go Bad
Even well-intentioned questions fail if:
| Situation | Bad Approach | Better Version |
|---|---|---|
| Someone's grieving | "How did they die?" | "What's your favorite story about them?" |
| Career changers | "Why leave a stable job?" | "What skills from your last role excite you in this new direction?" |
Adapting Questions Like a Pro
Reading cues determines your next question:
See their eyes light up? Lean in: "You loved that trip to Spain? What café moment sticks with you?"
Notice tension? Pivot gently: "Sounds complex - what part feels most manageable?"
Personality-Specific Adjustments
| Personality Type | Effective Questions | Questions to Avoid |
|---|---|---|
| Introverts | "What book/movie impacted you recently?" (Low pressure) | "Why so quiet?" (Puts spotlight on them) |
| Executives | "What industry shift are you preparing for?" (Strategic) | "How'd you get so rich?" (Vulgar) |
| Teenagers | "What's an app I probably don't know but should?" (Respects expertise) | "What do you want to be?" (Pressure-filled) |
The Forgotten Follow-Up Power
Great conversations chain questions. Example:
You: "What exhausted you this week?"
Them: "Preparing my daughter's science fair project"
You: "What was the coolest discovery you made while helping?" (Notice the pivot to them)
Them: "Actually, we learned vinegar cleans pennies better than soap!"
You: "Where else could you apply that surprise solution?"
See how it evolves? This works in job interviews too.
Your Go-To Question Library
Rapid-Fire Connection Starters
- "What's normal in your family that others find weird?"
- "What outdated skill do you still proudly use?"
- "When did you last change your mind about something important?"
Depth-Building Questions
- "What belief did you once hold tightly that you've since released?"
- "What pain taught you the most about yourself?"
- "Where do you find stillness in your busy days?"
FAQ: Your Question Concerns Addressed
How many questions are too many?
It's an interview if you're not sharing. I limit to 3 questions before offering my own story.
What if they give short answers?
Try: "Most people say [topic] is simple, but what's surprisingly complex about it?" Adds nuance.
How to recover from an awkward question?
Name it: "Wow, that came out wrong - I'm actually trying to ask about..." then rephrase.
Can questions work in text messages?
Differently. Avoid heavy ones. Try: "Saw [movie] last night - what film made you cry unexpectedly?"
Why This Matters Beyond Politeness
In our distracted world, asking thoughtful questions makes people feel seen. My barber told me last week: "You're the only customer who asks about my woodworking." We're wired to connect through curiosity. The best questions to ask someone aren't interrogation tactics - they're keys to human vaults. What will you unlock first?
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