25 Personal Questions to Ask a Guy You’re With

A woman using these personal questions to ask a guy, on a date with her boyfriend asking him questions as they hold hands.

It’s not always easy to get a guy to open up. Many guys guard their emotions more closely than girls. But when they do share, you get to see a whole new side of them you’ve never seen before. One of the easiest ways to get to know someone is by asking them questions. Once you’ve covered the basics through small talk, you can dive deeper and ask more personal questions.

These personal questions to ask a guy you’re with can help you get to know a different side of him. His answers will reveal a lot about him, from what he thinks about love to how he defines success. You might not always agree with him or see eye to eye about things, but you’ll definitely learn more about how his mind works and how he views the world.

The next time you’re alone with the guy you’re dating, ask him one of these questions and see where the conversation goes. While you probably don’t want to ask all 25 of them in one day—that would be intense—this list is a great place to start when you want to get more personal. Don’t forget to return the favor by sharing your answer, too.

1. What’s been your highest point in life so far?

2. What’s been your lowest point in life so far?

3. What makes you emotional?

4. What makes you stressed?

5. Do you believe in a higher power?

6. If you had the power to know the date of your death, would you want to know?

7. What are you most grateful for?

8. Is there anything you would change about yourself if you could?

9. Who inspires you the most?

10. Does being rich and famous appeal to you?

11. What’s the biggest risk you’ve ever taken?

12. What’s the biggest thing you’ve ever given up?

13. What’s the angriest you’ve ever been?

14. What’s the nicest thing you’ve ever done for somebody?

15. How would you describe your childhood?

16. Do you have any unresolved issues with your family?

17. How do your best friends describe you?

18. Do you trust easily?

19. What’s a secret you’ve never told anybody?

20. What did you learn from your last relationship?

21. How many girls have you told “I love you”?

22. Have you ever cheated in a relationship?

23. What is your greatest life goal?

24. What do you want for yourself in five years? In 10 years? 25 years?

25. Do you see me in your future?

Whether you’re still getting to know a guy or you’ve been with him for a while, these questions will help you get to know him in a new way. And best of all, they’ll lead to even more questions and deep conversations.

Elizabeth Entenman

Freelance Writer

Elizabeth is a freelance writer, editor, and advertising copywriter in Brooklyn. Right now, she’s probably somewhere Instagramming her dogs.

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