Questions You Should Ask Your Boyfriend’s Friends

A good rule of thumb in the dating world is to never date a guy who has no friends. Of course, there are always exceptions to any rule, but in general, friends are a necessary part of everyone’s life. His crew can also become part of your social circle as well as shed some light on what he’s like as a person. Here are some questions to ask your boyfriend’s friends if you get the chance.

  1. Is he the type of guy that other guys like? Guys aren’t wishy-washy about whether or not they like someone. They don’t worry about hurting someone’s feelings or being liked in return as much as girls do. So if your guy often seems to rub other guys the wrong way, there must be a reason.
  2. Does he have any female friends? Guys who are able to be platonic friends with girls — or better yet, guys who grew up with sisters — are always a little extra in touch with their feminine side. They care about the well-being of women and have probably been there for their female friends during rough times, so he’ll be able to do the same for you. While you could ask him this yourself, it’s one of those questions a guy’s friends can answer in more detail than he might be willing to divulge at first.
  3. Does he hold grudges? Is he the type of guy that will sulk forever because his friend didn’t invite him to a basketball game the one time? Will he dig his feet in and never be the first one to apologize? If he does that with his friends, you better believe he’ll do the exact same thing with you.
  4. Does he fight with his friends a lot? All friends have little fights once in a while, but are his friendships full of dramatic, end-of-the-world blow-out fights that make the Real Housewives look like two toddlers fighting over a rattle? Even worse if he’s actually been known to get into fistfights with his friends on more than one occasion.
  5. Does he have a mix of coupled-up friends and singles, or are they all still a bunch of frat dudebros who need to get drunk and party 24/7? You know where we’re going with this, and while this is one of those questions you definitely should ask his friends, you’ll want to find a much better way to ask it. You don’t want to offend them!
  6. Does he share things like inside jokes and regular traditions with his friends? Every time he sees a guy in a kilt, he immediately texts his buddy some inside joke from the time they backpacked through Europe together and spent a weekend in Scotland. That could mean he likes to share things with people, and he’s probably a lot of fun.
  7. How long have they all been friends? Does he still talk to some of the guys he went to high school with? Or even grade school? Chances are he’s a pretty good friend that other people like to keep around.
  8. Does he have more acquaintances or more close friends? He might be the type that prefers to keep people at arms length, so he has a bunch of different casual friend groups. But if he has a few really close buddies, you know he isn’t afraid to let people know the real him.
  9. How do his friends see you? If they don’t seem overly interested in making the effort to get to know you it might be because they don’t really think you’ll be sticking around for long. And that’s probably based your guy’s tendency to love ‘em and leave ‘em.
  10.  What’s his role in the friend group? Is he the reliable one that everyone calls when they need help with something? Or is he the perpetually single one they’re always trying to set up on dates, despite suspecting he’ll never really settle down. Better to know early on if you’re dating Joey Tribbiani, right?
By day, Courtney is a digital marketing copywriter living in Toronto, Canada. By night, she's a freelance lifestyle writer who, in addition to, contributes regularly to, IN Magazine, and SheBlogs Canada. Want to chat about relationships, Stephen King or your favorite true crime podcast/documentary/book? She's on Twitter @courtooo.