20 Questions To Ask The Guy In Your Life, Whether He's sNew Bae Or Not

20 Questions To Ask A Guy Whether He’s A New Bae Or Old

May 18, 2020 Updated May 26, 2020

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Most men aren’t exactly open books. You can be married to a man for decades and still have a hard time getting him to lock down on a favorite color. He may tell you about the girl who cheated on him, but do you know how he reacted to the end of that relationship? And what are your new guy’s goals… if he has any? When he says he wants a committed relationship, what does he really mean? Sometimes we’re great at projecting our feelings and aspirations onto our significant others, without really noticing that they want something different (or nothing at all).

If you’re a chatty girl, you’re probably with a guy who enjoys listening to you. That means you’ve probably mostly heard him chime in when he agrees with one of your big ideas. Especially if you haven’t known each other long, he might not be very comfortable contradicting you. “I want a house with a lot of land and quiet” might be met with, “Quiet is nice. I hate my apartment in the city.” But, he might be thinking about how he absolutely wouldn’t want to mow more than a quarter acre.

So, how do you get a guy (or anyone) to talk? For starters, you start listening. It also helps to ask him questions. These 20 questions might give you some more insight into your new bae. They’re linked to even more lists of questions and include related inquiries to help you further your conversation.

1. If you inherited a billion dollars, what would you do with your life?

2. What’s your most hated chore?

3. What’s something you always procrastinate on?

4. How do you like to spend your days off or what’s your idea of a perfect vacation?

So, on vacation are you more of a “do nothing” or a “do everything” kind of tourist?

5. Do you like kids and want kids?

6. What was your childhood like?

Expand with questions like: Did you take vacations? How did your parents discipline?

7. What do you want to do with your life?

Think: 5 year plans, 10 year plans

8. What do you hope your life looks like right before you die?

9. Do you have any expectations for yourself?

What are you hardest on yourself for when you mess up? What do you expect from others?

10. What’s the worst thing you’ve ever done?

Did you tell anyone? Did you apologize? Have you done anything to make it right or clear your conscience?

11. How important is religion to you?

What about your parents? How do you feel about other people’s take on religion?

12. What’s one thing you’ve never been good at?

Did you want to get better? What haven’t you tried, but hope to master some day?

13. What does the perfect relationship look like?

Is it marriage? Does that matter? Do people contribute equally on a financial level? Domestic level?

14. Who is your best friend?


15. Who is the most called/texted person in your contacts?

What do you talk about? How long are you usually conversing?

16. What’s the most difficult thing you’ve ever been through?

17. What’s your most useless “skill?”

If he says algebra, M.A.R.R.Y. H.I.M. — your future tenth grader will thank you.

18. What’s the biggest purchase you ever made?

What about the worst or best? What’s the last thing you charged on your credit card? Will you pay it right off or will it probably sit there for a while?

19. What’s something you were recently super proud about?

20. Who will you always make time for?

Why is that person most significant? Is there anyone else? What activity do you always take the time to do?

Some of these might sound exceptionally deep while others seem to only scratch the surface. The idea isn’t to stop at just this question but for the question to trigger a conversation. If what he’s most recently proud of is paying off a big credit card from his college years, that tells you a lot about his commitment and maturity.

Of course, there’s certainly nothing wrong with having hobbies and finding ways to unwind. But, if his most recent accomplishment is a great score at the golf course, where he’s played two rounds every weekend all spring and summer for the last three years? Well… The point is, even the superficial stuff can lead to longer conversations and deeper insight. The gist: Never stop asking questions, no matter how long you’ve been together.