56 Questions to Ask a Guy That Will Reveal If He's a Keeper or Not

56 Questions to Ask a Guy That Will Reveal If He’s a Keeper or Not

Posted by in Black Love Advice

Dating and relationships… With all the uncertainties and possibilities it can be a bit of an emotional rollercoaster.

The process of getting to know a person. The questions we ask ourselves about the future of the relationship. The advice our friends and family give us when we tell them our hopes or concerns about the person.

What does it all boil down to? The one thing we really want to know: Is this person “the one.”

Today we’re going to try to help you answer that question by giving you a list of questions to ask a guy that will uncover his values, how he really feels about you, and help uncover any red flags.

Now, this isn’t a compatibility test where you sit down and discuss each question and answer one by one.

Instead, it’s best if you slide one or two of these questions in every now and then during the course of a regular conversation.

Some of these questions are serious, and some are just for fun, but they are all questions that will reveal things about him that can help you determine if he’s the right man for you or not.

Sound good?

Okay, let’s start this questions to ask guys list with this standard inquiry that can reveal a lot about him.

1. What did you do last weekend?

How he spends his free time is probably how he’ll want to spend time with you. This question can also reveal what he values most in life. Hanging out with friends? Partying? Sports? Reading and educating himself?

This question can reveal a lot.

2. What do you like most about yourself?

56 Questions to Ask a Guy That Will Reveal If He's a Keeper or Not

Another thought-provoking question, this one goes to what he values the most about himself as a person. If his answers are superficial, it can be a red flag depending on the type of man you want to spend the rest of your life with.

3. How is your relationship with your mother?

The way a man treats his mother is a sign of how he’ll treat you in the long run.

If a man is disrespectful to his mother or when he speaks about her this is a major red flag.

4. How would you describe your childhood? Was it happy?

This question can get almost anyone to open up about the good and bad things in their past. Pay attention to his answers. Many of them could be indicators of how things will be if you decide to star a family with him.

5. Did you ever get cut from a sports team? How did you handle it?

This question isn’t meant to judge his athletic ability, but it’s a good way to see how he handles rejection.

6. What’s your number 1 money management tip?

Combining financial habits can be one of the most challenging parts of merging your lives. This question should give you some insight into how he manages his money without having a serious money talk.

7. Do you know any jokes?

This isn’t so much about whether your man can do stand-up comedy on the spot, but more about what he thinks is funny. If he answers with a joke that makes fun of someone’s gender, politics or sexual orientation, it can be a sign of deeper issues with his opinions on those things.

8. Are your grandparents still alive?

It’s important to find out if he makes time for his family. If he still has his grandparents, does he make an effort to talk to them or even call them?

This can show thoughtfulness and an ability to think about others.

9. What jobs have you held in the last five years?

This is a good way to see if he can get along with people and if he’s responsible. If he’s bouncing from job to job, he’s likely not going to carry his weight in the relationship.

10. What are your views on friends borrowing money from each other? When is the last time you borrowed money from someone?

Looking into his finances is one of the most important questions you have to ask when you’re looking for a man to commit too.

A man that constantly has to borrow money from you isn’t holding up his end of the bargain, and you should probably begin to question his motives for wanting to be in a relationship.

For those reasons, it’s important to find out if he regularly asks for cash from other people.

11. If you could have dinner with any one person from history, who would you choose?

This question might seem overdone, but it’s a good one for a reason.

This question can tell you what your man values most. He might answer a political figure, a religious leader or a deceased family member. All of these answers can tell you what he’s all about.

12. What are your vices?

We all have them, and you might as well know what his are sooner rather than later.

13. What type of drivers do you hate?

Does he hate speeders? What about the person who drives with their signal on? A man that can handle minor irritations on the road with patience is probably a keeper.

14. Do you own any guns?

Not taking sides here, but you need to be compatible on whether guns are going to be in your home or not.

15. What do you think of people who disagree with you on politics?

There’s going to be a day when you and your man disagree, so it’s good to know how he treats people that he disagrees with.

But not only that…

Having far differing political views can cause major issues in relationships. Just look at the video below of one woman who divorced her husband because he voted for Donald Trump.

16. Can you live without your phone?

We’re all attached to our phones these days, but some people are too attached. Make sure your guy has the right balance.

17. Crunchy vs. Smooth peanut butter?

There is definitely a right answer. It’s Nutella. 😂

18. What do you wish your parents had done differently?

This is a good question to get your man thinking about what has gone wrong and right in his life, as well as what he might want to do differently as a parent.

19. Are you a morning person or a night owl?

I’m not saying I believe it, but a new research report said that being a night owl might be a strong indicator of if someone is crazy or not. 😂

I’m not sure if that’s true, but being a morning person myself I can’t stand when my boyfriend lays in bed with the TV on all night lol.

20. Do you floss?

Dental bills later in life can really drag you down. Make sure your keeper is a flosser. Regular or minty fresh is fine. His choice.

21. Do you have any kids?

This is not something you want to find out after you commit. If he has kids, you have to make sure that he’s 100 percent responsible for them, and you have to decide if you want to be, too.

22. Do you want kids?

This question is one of the biggest. You have to get serious, and this one is about as serious as it gets.

23. If you have kids, what are your child support obligations and do you pay them on time?

You have to get down and dirty and do the math. Child support is a court order, and if your man doesn’t pay, he can go to jail.

24. When is the last time you went to church?

Is he a regular attendee, a Christmas and Easter kind of guy, or not at all? We’re not saying he has to be a deacon, but if you like going to church, you need common ground here.

25. Do you have pets?

Your man’s pets come with your man. If you have four dogs and he has four dogs, you either have a problem or not enough dogs 😂😂😂

26. Can you speak any other languages?

If he says yes, this is a good sign. It shows that your man is open to new cultures and people. It’s also a sign of intelligence.

27. Do you like living in this town?

If you like where you live, make sure your man isn’t setting up for a move. Trust me, it happens more often than you think.

28. What’s your career goals?

If you don’t ever want to leave your current city, it could be a problem if your significant other has a job that involves frequent transfers.

Just make sure that you’re compatible on this issue if you’re looking for a keeper.

29. Have you ever done a keg stand?

This question measures his glory, or his shame, depending on your view of it. Interpret his answer how you will.

30. Have you ever had a disagreement with a neighbor?

This question can tell you if he sweats the small stuff. It also reveals how he handles conflict.

31. Why didn’t your last relationship work out?

Sometimes it’s hard to tell if you’re getting an honest answer here, but this is still a good question to ask just the same.

Your man should offer some reflection and take responsibility for things that could have gone differently, or for the incompatibilities with his last partner.

32. How do you feel couples that live together should split bills and expenses?

You want a relationship, not a responsibility. You’re worth it, and you should never settle for a man who doesn’t stand on his own two feet. Simple as that. 💯

33. If you could quit your current job and do something else, what would you do?

This is a good way to reveal what is most important to your man. This is where he would put his time if it weren’t in his primary occupation, so whatever it is, it’s probably pretty important to him.

34. Have you ever been convicted of domestic violence, assault or battery?

If the answer is “yes,” you’re done. Break up, unfriend, remove from contacts and ignore. The answer is zip, zero, zilch, nada, no, under any circumstance.

35. Should women work?

This question might sound a little 1977ish, but some men have very strong opinions on this issue. A man’s not a keeper if he doesn’t respect you and your life choices, whatever they may be.

36. What’s your favorite sports team?

This is a particularly good question if you’re into sports yourself. This question makes sure that you don’t have a house divided during the NFL Playoffs lol.

37. Do you steal internet, music, cable or anything else?

This might seem like a little thing, but it can tell you a lot about your man’s honesty and personality.

38. Are you named after anyone?

You can learn a lot about a man’s family history by asking this question.

39. When you decide you don’t want something in your cart at the grocery store, do you put it back where it’s supposed to go or leave it?

If his answer is no, and you think that’s just lazy, it’s going to bother you forever.

40. What channel is your television on right now?

This question is not an opinion question. Statistics and probabilities tell us it’s a channel he often watches, so he values the subject matter.

41. How do you tip?

You should carefully observe your man when you go out to eat. If he’s rude to the waiter, it’s a problem.

Giving fair tips and being polite to servers reveals a lot about how he conducts himself on a daily basis.

42. Hot, Medium or Mild Salsa?

Because we all know you don’t want to have to buy two jars lol.

43. Do you have a criminal record?

Now we’re getting serious. Sometimes, what’s on a person’s record can prevent them from getting a job, housing, or financial aid.

It can also reveal substance abuse, anger, or other issues that are cause for concern.

44. How many beers do you usually drink when you go out?

A man that’s a keeper lives a life of moderation. There’s nothing wrong with having a few drinks. But you don’t want someone that gets sloppy drunk when they go out.

45. What is your favorite kind of beer?

If he says Big Bear, run ladies, run. If you’re from the hood, I know you understand lol.

46. How often do you workout? Do you have any fitness goals?

It’s important that your leading man takes care of his health, but it also shouldn’t be an obsession. Balance is an essential element of fitness, and of life.

47. When is the last time you spent more than $500 at once?

This question is a good one because it can reveal impulse purchases as well as what kinds of things he values the most.

48. Do you like pineapple on pizza?

You either love it, or you hate it, and you don’t want to fight about it.

49. Do you play video games?

56 Questions to Ask a Guy That Will Reveal If He's a Keeper or Not

Omg… I swear there’s nothing more frustrating than dating a serious gamer lol.

50. Do you have student loans?

With finances, it’s important to make sure that you get the entire picture. It’s okay if he has this kind of debt, especially if he’s a hardworking man who invested in himself and his future.

51. What are your biggest regrets?

Your man should have a thoughtful answer for this question. We all have regrets or things we would go back and do differently if we could. His answer will reveal a lot about his character.

52. What is the last thing you tried to fix around the house?

A keeper is willing to make an effort to maintain his household and his possessions. Even if he isn’t very handy, he will still make an effort.

53. Do you eat pork?

This is one of those things where either you do or you don’t. There’s no in between. Which can cause issues to arise during summer cookouts, grocery shopping, holiday’s, and evening dinner.

54. What’s the nicest compliment you ever received?

You can find out a lot about what your man values about himself and his identity with this question.

55. What apps do you have on your phone?

Asking this question can show you what your man likes to do in his free time. It can also tell you if you’re going to have to work harder to beat his high score in Words With Friends.

56. What do you like about me?

A keeper values your soul, your personality, and all that other good stuff on the inside. Make sure your man likes you for who you are. Beauty fades, a deep emotional connection doesn’t.


Finding a man that’s a keeper isn’t an easy task. Some questions, like finances, children and criminal history, are make-or-break questions when it comes to deciding whether to keep your new man or keep searching.

I hope these questions to ask a guy gave you some insight (and maybe a laugh or two.)

Once again, randomly slide a few of these questions into your regular conversations. But make sure you listen carefully to how he answers.

If you want to journey deeper into determining you and your man’s romantic compatibility make sure you check out our article “Compatibility Test: 255 Simple but Significant Questions for Couples!

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