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9 Deep Questions to Ask Your Best Friend’s Boyfriend & Read His Mind

Your best friend just got into a relationship, and you want to get to know the guy better. So, here are some questions to ask your best friend’s boyfriend.

Questions to Ask Your Best Friend's Boyfriend

Our friends are an extension of our family, and for some people, they are family. In this case, you want to be sure that anyone who enters into their life is there for the right reasons. And to do that, sometimes all you need are a few but loaded questions to ask your best friend’s boyfriend to know their intentions.

Girls, let’s face it, some guys can be shady. They say they’re ‘this’ and ‘that,’ and they fool everyone, but not you!

If you have a feeling about someone, a sense that something is a little ‘off,’ the chances are that it is. Of course, you could be acting a little over-protective too, so how are you supposed to know?

[Read: What makes a good friend? The 15 traits we desperately seek in a friend]

Interrogating your best friend’s boyfriend!

We’re not suggesting you tie him to a chair and shine a torch in his eyes until he caves, because we’re sure there are regulations or laws against that kind of thing. What we are suggesting is you subtly ask a few loaded questions, and figure out from his answers what you think.

All you’re doing is trying to ascertain that his intentions are good ones and that you’re not going to be picking up the pieces of a broken heart sometime in the next few months. 

Seeing your best friend in tears and hurting over some guy who couldn’t see how much of a catch she was is not pleasant for anyone, but a little investigative work could give you the head’s up you need. [Read: 22 early warning signs of a bad boyfriend you shouldn’t miss]

The most important questions to ask your best friend’s boyfriend 

Consider this part of your unspoken oath as a best friend – ‘thou shall not let your best friend date a rat,’ or something like that. The problem is, you need to do this in a way that doesn’t alert this guy to the interrogation. 

Be as nice as pie, but don’t make him think you’re flirting, because that could be a true disaster. Be nice, but be a little detached, that’s the best way.

So, what should you ask him? Here are some questions to ask your best friend’s boyfriend. [Read: 50 questions for a new relationship to predict your romantic future]

1. Ask what attracted them to your best friend

The approach you need to go with here is friendly yet firm. You need to let your friend’s boyfriend know that you are not his best friend and that you are never going to be because you have your eye on him. 

What you need to be, is civil. To do that, you can ask him what attracted him to your best friend. This will give you an idea of how serious he is.

If he answers in a non-committal way, that’s not good enough. ‘Erm’, and ‘uh’ is not an answer.

Watch his body language and see if he smiles when you ask. His face should take on a faraway look and he should be able to tell you exactly what it was, e.g. her smile, her laugh, her eyes. 

If he can’t tell you a single thing about why he was first drawn to your best friend, then he might just be acting a little flakey. Keep your eye on that one! [Read: 15 signs your friend is being used by a man and it’s time for her to ditch him]

2. Ask about his last relationship

We’re not suggesting you fire questions at him, like ‘are you married?’, ‘have you ever cheated on a girlfriend?’, because he’s likely to get annoyed and tell you to mind your own business. What you can do is ask in a light-hearted, borderline joking way.

‘Have you been single long?’, ‘have you ever been married?, ‘do you have any children?’ are all completely okay questions to ask. They give you information, but they’re not invasive because they’re questions that people ask in general conversation all the time. 

What you can do is check his facial reaction and body language when he tells you. That might give you extra information! [Read: 20 good questions to ask a guy and find out who he truly is]

It’s likely that your friend has told you a little about this already, e.g. he used to be married but he’s separated or divorced, or he was in a serious relationship for four years previously. See if what he tells you matches up with what you already know. 

If it doesn’t, that’s a huge red flag to be aware of. Maybe he’s embarrassed to open up to you because he doesn’t know you that well, but maybe he’s hiding something. Hopefully not. [Read: 34 very big red flags that most people in new relationships ignore]

3. Where do you think you’ll be in five years’ time?

He might feel like he’s edging towards job interview territory here, but hey, that’s fine! This is one of those questions to ask your best friend’s boyfriend that will show you what his future aspirations are, not necessarily with your friend but in terms of whether he is ready to settle down or not.

If he answers with a random line about sports or a pie in the sky idea, he’s either using diversion tactics, or he’s not serious.

If he says something about being married and having a child on the way, he could be a serious option for your friend! She doesn’t deserve someone who’s not ready, after all. [Read: 60 deep and fun get to know you questions to peek into their soul]

4. Are you wasting her time?

Go on, be direct! Do it in a funny way though, to avoid him standing up and walking straight back out again! Smile, laugh, and jokingly say ‘you do know I’m her friend and I’ve got her back, you’re not going to waste her time and hurt her, right?’ Check his reaction!

The idea with this one is that you’re doing it in a joking way, but you’re actually borderline serious.

He’ll know, he isn’t stupid after all, but you’re warning him subtly, without actually saying the words. Again, this is part of your best friend’s duty. [Read: How to recognize a guy who’s actually ready for a real relationship]

5. What would you do if you won the lottery?

This might sound like a silly question to ask your best friend’s boyfriend, but it’s actually a lot deeper than you think. Everyone has thought about what they would do if they suddenly came into a lot of money, but their answers can tell you a lot about a person.

If he answers with things like, “I’ll buy a yacht and spend all my money on booze and partying with my friends,” then that means he’s pretty shallow.

Sure, everyone likes to party and have a good time. But if he sounds like he’s going to blow all of his winnings on one big long party for the rest of his life, then maybe he’s not a quality guy. [Read: 25 deep questions to ask a guy and turn any guy into an open book]

On the other hand, if he answers along the lines of “I’ll start by investing at least half of it for my future and then buy a house” or “I’ll probably donate a lot of it to several of my favorite charities so I can help people,” then that shows that he’s pretty altruistic and he’s thinking about his future – not just being a party animal for the rest of his life. [Read: What age does a man emotionally mature? 19 signs a guy has grown a real pair]

6. What are your friends like?

Another one of the questions you can ask your friend’s boyfriend is about his friends. As the saying goes, “birds of a feather flock together.”

You want to ask this question to see what he has to say about his friends. He might start by telling you some crazy stories of things he has been through with them. Maybe he’ll tell you all about their drunken spring breaks and fraternity parties.

Or, he might tell you how smart they are and that they have a lot of goals in life. This is a better answer.

Again, there’s nothing wrong with partying. But you want your friend to have a stable guy with a good head on his shoulders, right? So, if he’s hanging around other responsible people, then he will offer stability in the relationship. [Read: What to do when a guy’s friends are a bad influence]

7. What is your family like? 

When you ask about his family, you can get a lot of information about him too. Ask where he grew up, what his parents do for a living, and if he has any siblings. There might be a difference between someone who grew up in a big city versus someone who grew up in a small town or on a farm.

Also, knowing what his parents do for a living is important. If his mom didn’t work, then maybe he expects his future wife to stay at home and raise the kids. And if your friend doesn’t want to do that, then there could be a big mismatch between the two of them.

Or if his parents are divorced, you might want to ask how it affected him and his own relationships. Some parents don’t handle it well, and it negatively affects their children. So, he might have some emotional trauma from his past that could seep into his relationship with your friend. [Read: Family oriented – The meaning and what it means to be this person]

8. Do you see yourself getting married and having kids someday?

Depending on your friend’s age, this is something that is important to know. If she’s young and wants to settle down and have kids, then she really needs to be with a man who wants the same thing. But if she doesn’t, it’s important to know that too.

It’s easier for you to ask this question than for her to do it. That’s because when she asks it, that can come across as her putting pressure on him to decide. She doesn’t want to appear clingy or like she’s chasing him.

So, when it comes from you, it is much less threatening to a guy – especially if they are newly dating.

9. Where would you put yourself on the political spectrum?

Now, most people would advise staying away from talking about politics. However, how someone views the world in terms of being conservative or liberal really affects how they live their life.

So, maybe your friend and her boyfriend haven’t talked about that yet. You can get the scoop and relay it to her. [Read: 23 reasons why good relationships end even if there are no red flags]

If your friend is very liberal but you find out that he’s very conservative, then their relationship might face a lot of challenges. When you’re in a relationship with someone, your values and world views need to align pretty well. So, if they don’t, they might not be very compatible in the long run. She should know sooner than later, don’t you think? 

What do you do if you find out something you’re not happy with?

There is the risk that by asking these questions you will actually have your concerns confirmed. Hopefully not, but it is a possibility and that is the whole point of actually using these questions to ask your best friend’s boyfriend. What do you do now?

You need to ascertain whether you should tell your friend or keep it to yourself. You need proof before you actually approach her because she’s probably in the first flushes of love, and as a result, she’s not going to believe anything which doesn’t have concrete proof attached to it. 

She could also react in a way you’re not expecting, e.g. accuse you of trying to ruin her relationship. [Read: 13 ways you may be ruining your friend’s relationship without realizing it]

It’s best to just wait and watch. If the information you’ve found is serious, okay go ahead and tell her, but you need to be 100% sure. Make it clear to your friend’s boyfriend that you have your eye on him if you have found something you’re not happy with.

For instance, if you asked him what first attracted him to your friend and he answers in a completely sketchy, non-committal way, fire back at him with a firm ‘she’s got so many amazing features, I’m surprised you can’t come up with a better answer.’

It tells him you’re onto him, and that could be enough to get him to step up. [Read: What is a best friend? 15 traits that make a friend a really good one]

If you ask him where he sees himself in five years and he says something random which doesn’t show a desire to settle down at all, you should fire back once more. Something like ‘you know she deserves the best, right?’ will give him the shove he hopefully needs.

Be firm and let him know that ‘hey buddy, I’m watching you.’ Telling your friend at this point is just going to cause problems between the two of you, and that’s never a good thing.

[Read: How to play a guy at his own game and make sure you win no matter what]

The whole point of coming up with questions to ask your best friend’s boyfriend isn’t to cause issues or problems, it’s to double-check that he is on the same page as her. She won’t know, because she’s got the honeymoon blinkers on. You’re the one with a clear head, so be her eyes and be on your guard on her behalf. 

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Nicky Curtis
Nicky Curtis
Having stumbled from one relationship drama to another throughout her 20s, Nicky is now somewhat of a guru in the crazy world of life and love. Telling it how i...
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