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

Your best friend’s just started dating, but you’re not sure about the guy? Here are four questions to ask your best friend’s boyfriend to suss him out!

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?

Interrogation, my friends, interrogation!

I’m not suggesting you tie them to a chair and shine a torch in their eyes until they cave, because I’m sure there are regulations or laws against that kind of thing. What I’m suggesting is you subtly ask a few loaded questions, and figure out from their answers what you think.

All you’re doing is trying to ascertain that their intentions are good ones, and that you’re not going to be picking up the pieces of a broken heart some time 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]

Four subtle 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 which doesn’t alert them to the interrogation. Be as nice as pie, but don’t make them 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 them?

#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 their best friend, and that you are never going to be, because you have your eye on them. What you need to be is civil. To do that, you can ask them what attracted them to your best friend. This will give you an idea of how serious they are.

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

Watch their body language and see if they smile when you ask. Their face should take on a far away look and they should be able to tell you exactly what it was, e.g. her smile, her laugh, her eyes. If they can’t tell you a single thing about why they were first drawn to your best friend, then they 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.

I’m 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 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: 17 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 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.

#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 gonna 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]

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 asking these questions. 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]

Personally, I would 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 be a good friend – The BFF code all girls must follow]

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.