9 Questions to Ask a Potential Boyfriend

This article is all about questions to ask a potential boyfriend.

Would your guy friend make a good boyfriend? We will discuss the questions you should ask and examine possible answers.

We know it has crossed your mind. He may be boyfriend material. But if you don’t know for sure, you may want to ask some questions.

Consider asking these questions only if you seriously thinks he is boyfriend material. Getting too deep in a plutonic relationship could go wrong if there’s no potential.

Before asking the man you had your eye on these questions, consider these factors way ahead of your pop quiz:

He’s good with your friends
He doesn’t flake
He’s your “fun” friend
He’s not too touch feely
You communicate with each other
He’s honest with you ⁽¹⁾

If he’s got all of these, then you are good to go.

We have 9 questions in this post. But know that you do not have ask all of them before you become official. You could ask a few now and more after the relationship develops.

Besides if things work out, you will be spending a lot of time together and talking a lot more. Instead on keeping those conversations on the surface, use these questions to take a deeper dive and explore more about who he is.

9 Solid questions to ask a potential boyfriend to know him on a deeper level

These questions are deep, but they do NOT cross that relationship line. So consider yourself safe. Ask these while you are hanging out or talking.

1. What is your biggest goal in life?

Get a sense of what they want to accomplish in life. This will also give you a chance to find what really gets them inspired and motivated.

Hearing someone answer this question is very intriguing and you will find that you are interested in what his true life goals are.

Alternative ways to ask this so that it seems less like a job interview are, ” What do you want to be when you grow up?” or “tell me you about the life you envision?”

2. What’s you favorite way to spend the weekend?

Time is the most valuable thing to spend. See what your prospect likes to do in his spare time and on the weekends. If you both get together, you will have an idea what he likes to do.

This is a way to find out what their favorite activities are. See if they have any hobbies that you find interesting or may have in common. Maybe it will be how you guys will spend time in the future.

Some casual ways to ask this question is to day “What are you doing this weekend?” or ” Any plans for the weekend?” This is a less formal way to ask if you don’t want it to be obvious.

3. Who’s your biggest role model?

This is a very important question because once you know the answer to this, you could follow up with more questions on why.

Once you know who this person is, you could do your own side investigation about their role model’s traits and abilities.

This is a hard one to come up with alternatives for, but it is such an important question to ask. Some people may ask this like “Who do you look up to?” or ” Who is your hero?”

4. What is the most spiritual thing you’ve ever experienced?

Okay, alright… This is the God question. What can we say, it it important for any potentially serious relationship.

This question could be intimidating to ask and to answer so, ask if you think it is appropriate for the timeline.

This could lead the conversation along the lines of ” Do you go to church?” or “Do you have a prayer life?” and other deeper conversation to get passed the surface.

5. What’s your greatest failure?

We all have them. Ask them to share theirs. Then share yours obviously. This is something he is probably working on with in himself, so it is valuable information.

We’ve asked this to some men and they literally are brutally honest. One guy said, “I am a cheater.” Which was a huge red flag, but we were amused at how direct he was about it.

Some creative ways to phrase this is to say, ” whats one thing in life you would re-do?” or “What’s something you are working to improve for yourself right now?” Or “Tell me about an embarrassing moment.”

6. Who in your life are you the closest to?

Because they will be an important part of your (potential) relationship. Is he a momma’s boy? Or does he spend alot of time with his friends. Is there a “girl” best friend in the picture.

This is a good question because this is who he will be around or will be in communication with through out the relationship. Might as well find out who they are asap.

Fun ways to ask it is to ask one of these: “Who’s your best friend.” or “Who is your oldest friend and “Who knows all of your secrets?”

7. What is your favorite family tradition?

This is a way to get some insight into his family members and their roles in his life. This could get into his favorite holidays or places to vacation.

This question gives a general look into how he feels about family in general and if that is important to him.

Some ways to ask this question is to say “What’s Your favorite thing about the holidays?” or “What is the most famous thing you mom or grandma cooks for Thanksgiving?”

8. What is your social life like? Are you popular or a loner?

This question is not as important, but if you are not around him that much this is a good thing to know. If you are around him a lot , then you probably do not need to ask this question.

Now I’m not saying stalk his Instagram, but check out his social media. Is he a popular guy (specifically with the ladies?). Or is his social media kind of dry?

His social life is an important factor in determining if he is a good fit for you. For example, is he on Tinder? If so, then he may not be looking for a relationship.

Are there a lot of girls on his social media profile? If so he may not want to make things official on their right away.

Ask him if he has a lot of friends. Does he consider himself a s a ladies man or a lone or somewhere in between.

9. What were some of the good and bad things about your last relationship?

Get to know as much as you can about his last relationship.This is how you will determine if you are going to shoot your shot. If you think he has passed the test then you will need to have a little knowledge about his ex and his past relationships.

For example, has he been in a long distance relationship. How long was his longest relationship. Has he ever been engaged? and much more.

Once you start asking questions like this, he will know that you are thinking of him in a more serious way. And if he is open about it, then more than likely you will have and honest relationship.