Because you’re not actually bad at socializing.
The Art of Asking Better Questions: Connecting Without the Awkwardness
Let’s be honest: icebreakers can feel painfully awkward in corporate settings. (No, HR, I’m not sharing my “roses and thorns” this year.) But in other contexts, they’re actually a fantastic way to connect. Asking thoughtful questions invites people to open up and share their experiences, helping to build trust and understanding. Licensed psychologist Luke Allen, PhD, highlights that this exchange of stories and perspectives is the foundation of meaningful relationships.
This might explain why the trend of “the one question I ask everyone” has gone viral on TikTok, as noted by therapist Kara Kays, LMFT. It taps into our universal desire to connect but offers a fun and simple way to do it.
Finding the Right Question Is Key
Of course, not every question is a winner. You don’t want to scare someone off with overly personal inquiries, but you also don’t want to bore them with a clichéd, “So, what are your hobbies?” According to Kays, the best questions strike a balance between being engaging and non-intrusive.
Take this example: asking, “What’s your favorite childhood memory?” is lighthearted and opens the door to meaningful storytelling. On the other hand, “Was your childhood a happy one?” may touch on similar themes but risks making the other person uncomfortable—or worse, bringing up past trauma. Thoughtful questions keep the conversation flowing while creating a safe space to share.
The trick? Keep it chill, open-ended, and focused on sparking joy or curiosity. These small shifts can transform an awkward exchange into a moment of genuine connection. So, the next time you’re sitting across from someone new, skip the generic small talk and dive into questions that truly bring their story to life.
# The “Let’s Skip The Small Talk” Collection
1. “What’s the most chaotic thing you’ve ever done that somehow worked out perfectly?”
*Better than asking about “adventures” – lets you gauge if they’re fun-chaotic or scary-chaotic*
2. “If your bank account suddenly had unlimited funds but you had to keep your current job, what would your life look like?”
*More interesting than the classic ‘what would you do with millions’ – reveals their actual dreams vs escape fantasies*
3. “Which historical figure would you want to grab coffee with, and what’s the one piece of modern technology you’d show them just to watch them freak out?”
*Tells you about their interests AND their sense of humor*
4. “What’s the weirdest compliment you’ve ever gotten that actually meant a lot to you?”
*Way more revealing than asking about regular compliments*
5. “What’s that one super specific life experience you think everybody needs to have, but when you explain it, people look at you like you’re crazy?”
*Shows what they value in a way that’s more fun than direct questions*
# The “Actually Deep Without Being Heavy” Section
6. “If you could instantly master any skill, but you had to live-stream your learning process to everyone you know, what would you choose?”
*Tests both ambition and humility in one go*
7. “What’s your most irrational talent – like something you’re inexplicably good at that has zero real-world application?”
*Better than asking about regular talents – everyone has these weird skills*
8. “What’s your most controversial opinion about breakfast foods?”
*Surprisingly revealing about someone’s personality while keeping it light*
9. “What’s the most ridiculous thing you’ve ever done to avoid a minor social interaction?”
*Gets at social preferences without awkward introvert/extrovert labels*
10. “If your Google search history had to testify as a character witness, what would be its opening statement?”
*Modern way to learn about someone’s real interests and concerns*
# The “Surprisingly Revealing” Collection
11. “What’s that one quote from a completely ridiculous source that actually changed your perspective on life?”
*Way better than asking about inspirational quotes – everyone has these*
12. “If your family dynamics were a Netflix show, what would critics say about the writing?”
*Gets family info while keeping it light*
13. “What’s the most elaborate form of self-care you’ve ever invented that would sound completely unhinged to anyone else?”
*More interesting than asking how people relax*
14. “What’s that one incredibly specific item in your home that has an entire emotional backstory but looks like literal trash to everyone else?”
*Gets at personal history in a unique way*
15. “What’s your most well-developed backup plan that you’ll probably never use but keep updating anyway?”
*Reveals hopes, fears, and dreams while keeping it fun*
# The “Actually Fun Follow-Ups” Section
16. “What’s the most chaotic good thing you’ve done this month?”
*Shows their values in action*
17. “If your past mistakes had a Greatest Hits album, what would be the lead single?”
*Gets at personal growth without the therapy vibes*
18. “What’s that one incredibly specific hill you’re willing to die on?”
*Perfect for seeing passion and principles in action*
19. “What’s the most unhinged thing you’ve done while procrastinating that turned out to be surprisingly productive?”
*Reveals work style and creativity*
20. “If your pet could write a tell-all book about you, what chapter would make your friends say ‘yeah, that tracks’?”
*Gets at authentic personality traits*
# The “Modern Life” Deep Cuts
21. “What’s your most justified toxic trait?”
*Everyone has these and the explanation reveals a lot*
22. “What’s that one life skill you’ve completely substituted with a weird workaround?”
*Shows problem-solving style and priorities*
23. “What’s your most specific 3 AM anxiety that actually came true but turned out fine?”
*Gets at fears and resilience while keeping it light*
24. “If your Spotify algorithm gained sentience, what would be its biggest concern about you?”
*Modern way to learn about emotional processing*
25. “What’s that one incredibly specific childhood memory that perfectly explains who you are as a person?”
*Gets at formative experiences without heavy background questions*
Responses (0 )