First Date. Women often ask a variety of seemingly unrelated questions, usually in an attempt to keep the conversation flowing and avoid awkward silences. Meanwhile, many men tend to stay quiet or simply don’t know what to say.
But here’s the good news: that awkwardness can be avoided with the right questions. Curious to know what those are and why they work?
First date, Let’s dive in.
The right questions can reveal even the most carefully hidden character traits. They turn a date into an engaging conversation rather than a job interview.
Smart First-Date Questions That Actually Tell You Something
1. What are your plans for next week?
This isn’t just small talk. It gives insight into how someone spends their time, their hobbies, their routine, and what they prioritize in life.
2. What’s something you’ve always wanted to try but haven’t yet?
The answers can be revealing. Some might dream of skydiving or visiting Africa. Others may not seem to have any goals at all—or worse, they might overshare intimate fantasies too early. Pay attention.
3. What’s a recent achievement you’re proud of?
This tells you what the person values and takes pride in. If the answer turns into a long monologue about themselves, that’s a red flag—they might be a little too into themselves, and that can show up in a relationship later.
4. Does anyone know you’re on this date right now?
Funny or telling. Are their 2,000 Instagram followers in the loop? Did they tell their mom? Or maybe no one at all? This question gives insight into how they view early-stage relationships.
5. What dating or relationship advice would you give your high school self?
If they say something like, “Date multiple people at once,” you might want to think twice. It could mean they’re still keeping backup options now.
6. What do you like—and dislike—about dating?
Seems like a generic question, but answers can be surprisingly telling. Some people love exploring new places; others find dating emotionally exhausting.
7. What day would you want to relive?
A powerful window into someone’s values. It could be the day they climbed Everest—or their wildest high school party.
8. What are you known for among your friends?
Maybe they’re the person who always shows up when needed… or the one who downs two liters of beer in 20 seconds. Either way, listen closely to both the content and tone.
9. Which stereotype about men/women do you dislike the most?
This question digs into their beliefs about gender roles and expectations in relationships. It’s also a chance to see if your values align.
10. If you couldn’t work, what would you do with your time?
Most people don’t have their dream job. This question reveals passions, ambitions—or lack thereof.
11. What freaks you out?
Public speaking? Snakes? Clowns? It’s a lighthearted way to understand fears and vulnerabilities.
Bonus: it’s a great opportunity to share your own.
12. What’s a total dealbreaker for you?
This one’s important. Some people hate lying, others judge based on past relationships. It tells you what they won’t tolerate.
13. What’s the weirdest or most embarrassing thing you’ve ever Googled?
A humorous way to test their sense of humor—and how open they’re willing to be. Be prepared for anything!
14. Do you have any emotional “scars” from your past?
Don’t ask this right away, but if the moment feels right, it can open up a meaningful conversation. Just be aware—some answers may surprise you.
15. What’s the best advice you’ve ever given someone?
People often reveal their own struggles through the advice they give others. You might learn what they’re still working through today.
16. Do you believe men and women can be just friends?
This question can say a lot about how someone sees boundaries and opposite-sex friendships—especially if something in the relationship goes south.
17. What’s the biggest misconception people have about you?
Do people think they’re arrogant, careless, too serious? Ask why they think that impression exists—you might get an interesting story in return.
18. What’s a job you could never do?
Great for understanding someone’s dislikes, limits, or even ethical values. They may hate routine, or refuse to harm animals. It all paints a picture.
19. Where’s a place you love so much you’d go back again and again?
Whether it’s a park, a movie theater, or a quiet café, this shows how they relax—and if your vibes align.
20. How did you meet your best friend?
There’s an old saying: “Show me your friends, and I’ll show you who you are.” This question gives a wider view of their values and loyalty.
21. What’s something most people are afraid to do, but you’re not?
This is where you might learn about their courage, ambitions, or confidence. Are they humble or full of ego? Their tone will tell you.
22. What’s your most vivid childhood memory?
Childhood stories can say a lot about how someone sees the world—and how they became who they are today. Do you have any go-to questions that help you read a person like a book on a first date?
Share them in the comments!
Have a great day!
