40 Get-To-Know-You Questions To Ask A Guy To See If You’re Compatible

Photo: getty
40 'Get To Know You' Questions To Ask A Guy On A First Date That Reveal Your Love & Relationship Compatibility
Love

When you're on a first date and trying to figure out your potential love and relationship compatibility with a partner, trying to strike a balance between asking insightful "get to know you" questions and making a guy feel like he's under an FBI interrogation can be difficult.

However, when you head out on a first date equipped with some fun questions to ask the guy you're meeting, you can have a more enjoyable and relaxed time getting to know someone new and avoid awkward silences, too.

RELATED: 21 Best First Date Questions That Ensure There's Never An Awkward Silence

While you're eager to get to know all you can about this new guy to see if you two are compatible, barraging a man with a list of questions to "vet" him in order to discover if he's worthy of a second date is no way to begin a happy relationship and will never work.

Why not? For one thing, it's a terrible turn off for men. Who wants to be interrogated? Not me — would you? In addition, first date questions like that often attempt to get at private information you have no right to know upfront.

For example, if you ask a man why he got divorced, do you think he'll openly admit he messed up? Nope. So, what did you learn with that question? Not much, except that you made him uncomfortable — which won't get you a second date.

You need to also think about the impact of the questions you ask someone on a first date.

Other women focus on being nice, smiling and nodding, hoping the guy will like her. You listen intently and add in some of your own thoughts and point of view. The goal is to show interest and ask a few get-to-know-you questions.

Then, if the man doesn't ask you anything, you hope he'll be more curious next time and want to get to know you better on the second date. This strategy won't help you connect with a quality man either, since you'll come across as bland and dull. Nice is not a standout descriptor. Do you like nice guys? Not likely.

Neither method is recommended for your first encounter with a new guy. Remember, you only get one chance to make a good impression, and that first date is also a time to check if the chemistry is good. It's not just your fact-finding mission. He's investigating you, too! If you hope for a second date and that he wants to know more about you, you'll have to do better.

That's why it's smart to plan ahead and have a few juicy "get to know you" questions in your back pocket that help you take the conversation into more interesting places. You want to be fun to talk with and bring out his personality, so you can see who he really is without grilling him.

Of course, your first priority is to discover if you have a connection and can hold a decent conversation. Do you get each other and understand his sense of humor? But while you're at it, why not find out a little about what makes him tick? You want to know how he thinks about life to help you decide if he has the potential for long-term compatibility.

These questions to get to know someone fall into eight basic categories. Don't even think about asking them all! The variety lets you pick and choose the ones that will help you learn what you want to know. And they may change based on what your date talks about on his own.

Try different options to see how they land and what delivers the best insights for you. Make it fun and enjoy the discussion — that's the way to get a second date.

Here are 40 "get to know you" questions to ask a guy on a first date to find out if he has potential for love and relationship compatibility:

Who does he admire?

Who does your date see himself aligned with? What public figure best reflects the qualities he wants to embody? This can be very telling, but don't make too much of it if he can't quickly choose someone.

1. Dead, alive or fictional, who is the one person you wish you could have dinner with?

2. What public personality has influenced you most?

3. Name a famous person you admire and why.

4. Who inspires you?

What holds his interest?

His answers to these questions let you know what captivates him. Similar interests can help you bond or you can share your differing interests and learn from each other.

5. What do you like to read?

6. Tell me a favorite movie or TV show.

7. How would you spend a rainy Sunday afternoon?

8. What do you enjoy in your free time?

What's his personal history?

Want to know about his youth and growing up? These five questions help you find out about how he views his childhood.

9. What were you like as a kid?

10. Where did you grow up?

11. What’s the worst thing you got caught doing as a child?

12. Did you play a musical instrument in school?

13. Did you play a sport in school and what was it?

What are his passions?

What makes this guy tick? Discover what he's passionate about to get to know him better. When a man talks about his passions, you get to see what lights him up and where his energy goes.

14. If you won $10 million, what would you do with yourself every day after the thrill wore off?

15. Have you ever volunteered for a charity and what was it?

16. What are you thinking about learning next?

17. What’s your most important goal right now?

18. What are you passionate about?

RELATED: The 5 Best Conversation Starters & Unique Questions To Ask Someone In Order To Get To Know Them

Does he have a sense of adventure?

Check out where he wants to live or visit, and you'll learn a lot about who he is, his dreams and plans.

19. What's your happy place?

20. What was the best vacation you ever had?

21. Name one place would you like to go back to.

22. What are you curious to try but haven't done it yet?

23. If you could live anywhere in the world, where would that be?

24. What's the strangest thing you ever ate?

What's his personality like?

Answers to these questions will help you discover how your date sees himself. The more you uncover about him, the better you can determine if he's the kind of guy you've been dreaming of.

25. What makes you smile?

26. What's the best advice you've ever gotten?

27. Tell me something I'd never guess about you.

28. Give me three random, fun facts about yourself.

29. What do you think is really annoying?

30. Name one thing you like best about yourself.

31. What makes you feel proud?

How does he live?

If you're curious about his lifestyle, try a question or two from this group. Sometimes compatibility boils down to having similar sleeping and eating habits or shared views on a healthy lifestyle.

32. If you were on a desert island with only three foods to eat, what would they be?

33. What's your favorite local restaurant?

33. How do you stay fit?

34. How do you destress?

35. Are you a morning person or a late-night owl?

What does he value about relationships?

Now we are getting down to what counts most! What does he value about his relationships? These last questions will be very telling and help you find out what matters to him about the people he's closest to.

36. Tell me about your best friend.

37. What do you like most about your best friend?

38. Tell me about your family.

39. Do you believe in love?

40 What's your biggest deal breaker

Now that you've got plenty of questions to get to know someone, here's something for you to consider. Anything you ask, you better have an answer for yourself! Don't get caught off guard.

Give these questions some serious thought so you can let your responses roll off your tongue like you say them every day. The last thing you want is to be surprised and sit there "umm"-ing as you grapple for an answer.

Relax and enjoy the process of meeting new men. You never know what you might learn or who you might meet. And you never know who your date might introduce you to.

In case you two aren't right for each other romantically, friendship can be a great option. Extending your social circle is always good because the more people you know, the better your chances for finding the lasting love you dream of.

RELATED: 100 'Getting To Know You' Questions To Ask On First Dates

Subscribe to YourTango's newsletter to keep up with us for FREE

- Our best articles delivered straight to your inbox
- The latest in entertainment and news
- Daily horoscopes and love advice

For seventeen years, Ronnie Ann Ryan has been a love and dating coach for women who has helped thousands of successful single women with hot careers (but a chilly love life) find lasting love. Watch her free masterclass to discover 5 Astonishingly Simple Ways to Find “The One.”