What Should I Do About My Boyfriend’s Awful Taste in Friends?

I am dating a pretty cool guy who is very sweet and attentive. I like him a lot and can see us becoming a solid couple. He says he wants us to be together in the longterm too. The only thing I’m having a tough time with are his friends. He always builds them up before I meet them by saying: “You’re just gonna love so-and-so”, and then when I meet the friend, they’re mildly offensive and nothing like him.

So far, almost every single one of them is kind of a prick and a player. The one he considers his closest friend is a self-proclaimed womanizer whom I’d describe as lazy and opportunistic. This friend hardly works (I think he’s a part-time telemarketer), lives beyond his means, and doesn’t mind telling bald-faced lies about himself to impress the ladies. My boyfriend shakes his head disapprovingly and acts like he just tolerates his buddy’s shenanigans, but at the same time, he’s obviously in awe of his friend’s lifestyle because I hear him complimenting his friend on his lavish purchases and hot dates.

The rest of his pals don’t get much better. One is so rude to waiters and cab drivers to the point that it’s embarrassing to be with him in public. Another seems to enjoy bringing up the sordid details about my boyfriend and his ex-girlfriends in front of me, like he wants to get a rise out of me or something. One guy makes me feel like I have to defend everything I do, as in “What would behoove you to take a trip there? Why would you invest money in that junk? Why do you listen to that crap?” Another one admits he “collects” hot women in his life almost as a hobby. And of course there’s always-loud-and-drunk guy; we can’t forget him.

My question to you is… is the company my boyfriend keeps an indicator of something wrong with him? I respect him, but I have a really hard time liking his friends, let alone respecting them. I can’t help but wonder why he doesn’t hang out with nicer guys. I admit that I feel a little threatened that they might be bad influences on him. Or that he really is like them, but is putting on a show for me until the day he reveals his true colors. I’m also worried that I’m going to have to end up grinning and bearing my way through many nights of their company.

I don’t even know how to raise my concerns to him about his friends without coming off like the bitch who’s trying to turn him against them.

I am starting to consider ending our relationship; that’s how uncomfortable I feel about his choice of friends.

Got any advice for me on this one, Evan?

Ready for Lasting Love?
Ready for Lasting Love?


Dear Valerie,

There were two chapters that addressed this in my book, Why You’re Still Single: Things Your Friends Would Tell You If You Promised Not to Get Mad.

Sometimes your friends actually are toxic.

One was called “Boyfriends with Boy (and Girl) Friends”. The other was called “Your Friends May Be Hazardous to Your Health”, but it was cut because the publisher didn’t think that women could handle this bit of controversy: sometimes your friends actually are toxic.

Thankfully, it’s easier for women to discuss HIS terrible friends than their own. So let’s run with that for a bit….

Cliché has it that we are the company that we keep. I would largely disagree. I went to a college where 10% of the school was Jewish, yet my five closest friends turned out to be Northeast Jews. I didn’t look for them, didn’t do a single religious thing in four years. But somehow we found each other based on similar interests, backgrounds, and humor.

But let’s say fifteen years ago, I joined a fraternity, had my friends chosen for me, bonded with them over drinking and girls, and still kept in touch. We graduate, move to the nearest big city and start our lives. They’d still be my closest friends. After all, we’d have a lot of history. We’ve got inside jokes, shared experiences, and a common bond that is hard to replicate in the “real world”.

Unfortunately, some of those guys never grew out of being frat boys. And although, in my maturation, I can probably see their deficiencies, I don’t want to dwell on them. They’re guys being guys. Yeah, they can be kind of crude, but they’re not malicious. At least not to me — although I wouldn’t want to necessarily set up ‘em up with my sister.

Old friends are sort of like family. They’ve been with you for so long, it’s almost like you didn’t choose them.

In that regard, old friends are sort of like family. They’ve been with you for so long, it’s almost like you didn’t choose them. And if they’re your core group, it’s pretty hard to jettison them unless you have a new group waiting to embrace you. So you put up with them, willfully blind yourself to their flaws, and hope that you don’t get tarnished by association. This could be what your boyfriend’s going through.


All of this blather hasn’t acknowledge one important thing, Valerie, which is that your feelings are perfectly valid. There’s no defending such a boorish group of people. That said, you’re going to have a devil of a time trying to make your boyfriend disown his friends. Like losing weight or quitting smoking, ditching your crowd is a pretty big decision — and it’s a conclusion that he has to draw himself.

As for how you should proceed? I’d try to assume the most non-judgmental tone and tell him simply and unemotionally that his guy friends make you feel uncomfortable. Emphasize that you’re not trying to divide him from them, but rather that you want to understand why he’s so loyal to them. Always let him know that he’s not WRONG, but that you just think he’s very different than his friends, and have trouble seeing what they have in common. Let HIM conclude that they’re toxic, instead of you being the judge, jury and executioner of their fates.

Let HIM conclude that they’re toxic, instead of you being the judge, jury and executioner of their fates.

Assuming that your boyfriend is, in fact, more evolved than his friends, he probably shares a few of your thoughts but has chosen not to act on them. And if he can at least admit that perhaps his good friends aren’t that good at all, you at least have an opening from which you can work.

A reasonable compromise might be you hanging out with your girlfriends on the nights he hangs out with the guys. That way you’re not forcing him to do anything, but are making a statement all the same.

Regardless, your primary goal shouldn’t be to force your boyfriend to dump his friends; it should be to understand why they are his friends.

In doing so, you will understand your boyfriend and his crowd much better, and determine your next course of action. Please let me (and all our readers) know how it goes.