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

group of guys celebrating

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?


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.



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  1. 1

    perhaps you could post that lost chapter on this blog evan. it might make for some interesting discussions

    1. 1.1

      I had a boyfriend whose friends are all completely immature, unemployed, pot heads, alcoholics.    If your boyfriend hangs out with them regularly beware.   Birds of a feather flock together.    Life with him and all the bad influences was a nightmare.   I wouldn’t waste my time if I were you.

  2. 2

    Evan wrote:
    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.

    Sounds like an interesting ( juicy ) addition to your site if you don’t have other plans for it.

  3. 3

    I’m curious on just how his friends are impacting their relationship if at all. She seems to still be interested in him and his personal qualities despite the qualities of his friends. I’d also be curious on what her perception would be if they were further along in their relationship and she had similar issues with his family too.

    I just think people are way too distracted by things external to their relationship. Their energy would be better expended on things the relationship itself.

    1. 3.1

      You don’t understand what she means by this, do you? It’s not the fact that her man’s friends are rude to her, it’s the fact that they could ruin the relationship. I’ve been with a guy who’s friend tried making him break up with me all because I didn’t like his friend. I had great reasons to not like any of his friends. One of them used my boyfriend to steal things; he also tried to make him do drugs and drink alcohol (I do NOT support alcohol what-so-ever because of my family). His friend that tried to make him break up with me accused him of stealing $40 from him. These people are not real friends. Just because they have “history” or “similarities” doesn’t mean squat. Boys are so gullible and desperate for friends and/or attention. True friends won’t make you change your mind or do bad things. In reality, boys (not men) are the sensitive and vulnerable.

      1. 3.1.1

        Soooooo true!

    2. 3.2

      Sometimes your partners friends can be hazardous to your relationship if they don’t respect your relationship.

      I have an issue with my boyfriends friends being into hard drugs which I feel strongly against and I don’t want to be in that environment nor do I feel comfortable with my boyfriend hanging out with them when they are acting like frat boys. They are 27 years old. I then become the party pooper and they disrespect me and discourage our relationship. They want their wing man back so they can continue acting like they are 16 when they should be growing up and buying a house.

      Not to mention his best friend is just an awful person period but they started hanging out as kids when the freindship was platonic. And I love my boyfriends family. They don’t care for his friends either. He’s a good person. He’s not like them and they are not good for him.

  4. 4

    I can see why see wouldn’t be so keen to hang out with his friends, but really, how often does she HAVE to? If she’s going to go with the premise his friends will be a bad influence on him, she might as well just let him go now given that she doesn’t trust his own judgement.

    If they ended up staying together, they would in time likely have friends they both enjoyed spending time with and he could keep “his boys” to hang with on his own while she did her own thing. This seems like somewhat of a trivial thing to break up over, but if it bothers her this much now, it might just worsen the more their lives become entwined and she feels she should have more of a ‘say so’ in who he/they spend their time with.

  5. 5

    I’d like to know how old is Valerie’s boyfriend; is he a couple of years out of college or a few years out? and where are these friends from – his past or a current gang he hangs out with? They might be some old frat buddies he’ll grow out of. But if he’s 38 and still hanging with this crowd I’d wonder.

    Secondly, Evan it sounds like you’re saying the company you keep IS a reflection of yourself. On the one hand, in true life you formed a self-selected group of friends based on (presumably) shared cultural values, humor, etc., which is a more realistic indicator of true friendship. In your second example you say you’d call frat brothers your ‘best friends’ even though the only things you would have shared would have been part of the same club and you would probably all have moved on by now. The latter is not as realistic a view of true ‘friends’, and if this is the type of situation Valerie’s boyfriend is in then I’d hope he grows out of it for her sake

    Valerie, I’d say be patient and be honest. Evan offers some good advice here on how to communicate. you’re not going to get along with EVERY one of your boyfriend’s buddies, but you also have to be honest with him.

  6. 6

    $Francisco, Selena. Excellent points!

    downtowngal, I interpreted Evan as saying that the newer people in your life are a reflection of who you are ( I agree ), but that is not necessarily true of older friends who you stay friends with because of you have a shared history ( like family ) with them.

    Valerie, I can feel your pain. Because of mutual friends I have had to endure more than one evening tolerating the loud drunk, the contrarian know-it-all and my all time favorite – the stoner conspiracy theorist.

    LOL! It makes you appreciate a dull ordinary day at work with you coworkers doesn’t it ? 🙂

  7. 7

    QUOTE: “All of this blather hasn’t acknowledge one important thing, Valerie, which is that your feelings are perfectly valid. ”

    You know, Evan, I think this is one of the reasons you’re so popular and successful. It doesn’t crush your ego to validate a woman’s feelings.

    Men having trouble dating should take note.

    But they won’t, because someone — especially a woman *gasp* — has dared to actually offer advice/make a suggestion *gasp, choke* that might improve their success.

    (OT: This might actually be the OP’s issue too, in a way; I’m wondering what she thinks. Actually, I think I know what she thinks, since she’d rather end the relationship than say something.)

  8. 8

    $francisco, Selena & downtowngal all had excellent points. Evan’s response was excellent also. I wonder if Valerie isn’t engaging in some unconscious effort to see if her boyfriend would choose his friends over her. One can’t tell from her post, but I have to wonder what it is the real issue here – she’s thinking of dumping him because of his friends? Seems like an extreme response to a small problem, one that has nothing to do with their relationship at its essence.

  9. 9

    “Seems like an extreme response to a small problem, one that has nothing to do with their relationship at its essence.”

    Now this? This is that dismissive, invalidating stuff that I mentioned that Evan doesn’t do.

    It’s a well-known axiom that “people judge you by the company you keep.”

    Friends and family exert an enormous influence on relationships. That influence increases as the relationship develops — particularly in the case of the friends/family that both parties had before the relationship started.

    So my guess is that the OP is trying to evaluate their future impact on the relationship as well as their present impact — not to speak of the fact that she’s already said she doesn’t like them.

    It’s not extreme at all.

    If it were me (and I know it’s not), I wouldn’t listen to Verbosity’s amorphous yammerings about “…essence…”, OP. He’s already told the whole blog he plans to remain single for the rest of his life.

  10. 10


    The original poster wrote that her boyfriend does not act like his friends and does not seem to be influenced by them. Why is it dismissive to suggest a simple solution like her taking a girl’s night out with her crew when her boyfriend wants to spend time with his friends?

    1. 10.1

      He may not act like them in the first few months, but believe me, he will eventually. And once his friends are intertwined with OP’s friends, stuff can get complicated. Also, there are some people who will drag you into their dramatic bullshit even if you didn’t ask to be included. These friends, the ones who are acting loud and obnoxious and who have no common sense or compassion for others, they will get under your skin.

      Another part of it is that if they aren’t supportive friends, you will hear about it. Naturally you will be upset for your SO because you want the best for them and you want them to be around people who raise them up, not people who drag them down. But because they have been ‘friends’ for so long (actually meaning people who you say rude things to and don’t support – according to some people) they can’t bring themselves to cut these people out. In turn, you end up being the person who is there to deal with the negativity  every single time they get let down by their friends(which is consistent), and yet your SO doesn’t listen to you when you explain why you think these people are toxic.

      Oh and lets not forget, they WILL find a way to make you feel bad too. Even when you have literally done nothing to cause them to even speak your name. They just love bringing every person in their lives down.

      To say that the relationships that an SO holds with others won’t affect your relationship with them is not true. These people are a huge part of their life, and they most likely always will be. Not only that, but they will have a direct influence on your SO, such as anyone’s friends have on them.

  11. 11


    Did you ever watch the old sitcom “Leave It To Beaver”? The neighborhood kid, Eddie Haskell, was often the impetus of getting the poor Beav into trouble for going along with his schemes. The Beav was basically naive and didn’t catch on to what Eddie was reeling him into until too late. Again and again. The Beav ofcourse was a child.

    As a adults we are more cognizant of our choices, good and bad, regardless of the influence of our friends. If Harry jumps off a cliff are we going to follow him? Mm, no. But if we did follow him for whatever reason, the we do so knowing it’s our on folly. I don’t know about you, but I’ve had a number of diverse friends over the decades–and not all of them would I choose to be like, though I appreciated them as individuals anyway.

    Valerie has said she doesn’t like her boyfriends friends, okay so she doesn’t HAVE TO hang out with them if she doesn’t want to–at least not often anyway. It’s her boyfriend she has choose whether to like or not, that’s the essence and I agree with Verbosity. If she thinks her boyfriend is going to jump off cliffs/cheat/get drunk/develop the habit of arguing controversial opinions just because his friends do then obviously he’s not the guy for her. This based on just what she thinks he MIGHT do.

    Personally, I choose my boyfriends on how much I like them as persons. Some of their friends I can just enjoy laughing about.

  12. 12

    This reminded me of something a previous bf and I did once. We started out talking about how everyone has “a thing”, meaning flaw. We ended up going down the list of all our friends and acquaintances as to what we thought their “thing” was. Sam-addicted to tv poker, Mike-pot smoker, Jim-picks fights when drunk, Ang-always forgets to pay water bill, Kathy–problem spender.. and on and on. It was amazing and amusing how we could find some flaw no matter how trivial, in everyone we knew–most especially ourselves ofcourse!

    But no matter what, these people still had value to us–we liked them flaws and all.

  13. 13

    Good last post Selena.

  14. 14
    valerie (original post author)

    Thanks for the differing perspectives, everybody. I can completely understand that
    you are not the company you keep, and that some friends you just stick
    with out of nostalgia. That said, my fears did come to pass, and I do wish I’d listened to my doubts earlier.

    All told, I never once said a thing to this guy about his friends, because I was thoroughly paranoid that my doing so would be subject to the unfair speculation (a-la-Verbosity) that I was “engaging in some unconscious effort to see if [my] boyfriend would choose his friends over [me]”. I kept my feelings to myself entirely. I tried to have plans with my girlfriends
    when it looked like I’d be spending time with his friends. I was cordial to his pals when in their company. Still, I started to notice my boyfriend’s behavior changing, presumably because he was starting to get comfortable and didn’t feel the need to be on his best behavior around me.

    Here is the short list: He got behind the wheel and drove home stinking drunk after a night out with his buddies. He lied to help his best friend cover for
    cheating on a girlfriend. He loaned the same guy “get-laid-with-someone-new”
    money that he’ll probably never see again. He joined in when his friend ridiculed an opinion of mine (which he happened to agree with, by the way). Finally, we had to leave early from an expensive concert I paid for because his loud/drunk friend got
    ejected; afterwards, he wasn’t the least bit apologetic about it.

    Perhaps the mature thing would have been to have the discussion about his friends at least once to give him the chance to say something on his own behalf. But
    I guess I just realized I really didn’t have the energy or will to make things work with this man. I didn’t feel it would be worth it to criticize him if I was just going to break up with him anyway.

    So, if there’s anything to take away from this experience, maybe the absence of healthy friendships shouldn’t count against a potential mate. But from now on, I think I’m going to add the quality of one’s friendships (a subjective assessment, I know) to my list of Highly Desirable Traits In A Man from now on.


    1. 14.1

      Hi Valerie,
      Finally, I have found someone who went through the same relationship situation as me.   I just wish and regret that I invested and wasted 5 years of my life. It got to the point that I had to break up with him and he got tired of living two  separate  lives because I refused to hang out around his counter-productive friends. So that meant he had his life with me and lived a  separate  life with his friend’s. It was important to him that I was able to hang around with his friends, too in our relationship. Constantly, I was ridiculed from his friend’s or they would use him for his money, etc like your story, too.
      You can be proud of yourself, Valerie and thank you, for sharing your story, that literally helped me out it this trying time for me.

  15. 15
    Evan Marc Katz

    Thanks, Valerie. Sorry it worked out that way, but it looks like your guy WAS the company he kept. Glad you learned something from the experience.

  16. 16
    Hot Alpha Female

    Hi Valerie,
    I’m really sorry to hear that about your guy. But i think that you did the right thing.

    Sometimes it can be confusing when it comes to a guy friends. Because as a general rule YOU ARE like the people you hang around.

    My initial response to your post was actually .. you should accept his friends the way that they are .. or not date him at all.

    And i was going to bring up a point about not changing him and what not.

    I’m very glad that you did everything you could to respect who he is as a person and I’m glad that you had the self esteem to know that you deserve so much better!!

    You go girl

    Hot Alpha Female


  17. 17

    Hey, Steve –

    “The original poster wrote that her boyfriend does not act like his friends and does not seem to be influenced by them”

    You just gonna let this hang on out there? Still so sure this is the case?

    Valerie, I’m sorry for what happened. I think women in this culture are so influenced to bite their tongues, and not comment on the anti-social (and often dangerous bordering on fatal, like the drunk driving thing) to avoid being branded “not nice”, or at worst, “the bitch”.

    All for pointing out that someone else’s behavior might just suck, to the point of wreaking horrible havoc in other people’s lives. (People they care about, even! Frequently those people get the worst of it!) ‘Cause you can’t tell them anything; they’re always right, can’t tell THEM what to do!!!

    I hope your dynamics are different next time.

  18. 18

    To be fair, Valerie’s initial letter did indicate that her bf was NOT like his friends, so there wasn’t reason to think he was unduly influenced by them. It would appear he fell right into their mentality though, once he became comfortable enough around her to not be on his best behavior. Go figure.

    If anything, this might be a case of Valerie’s gut instincts being on target, but who knows? What if it had gone the other way? A cautionary tale to be sure.

  19. 19
    valerie (original post author)

    Honestly, I think everything happened rather predictably. Even if my ex-guy wasn’t exhibiting behavior like his pals, I thought it unlikely that he could be so close to these friends and not share some of their worse qualities.

    I’m still glad I held my tongue and just broke things off. (I think I was fairly balanced in the way I told him that I was simply looking for something different in a relationship.) I believe it would have been an uphill battle to change the situation.

    I think the other lesson I learned here was to listen to my gut, especially when it seems to have common sense on its side.

  20. 20

    WOW – this is the exact situation i have just come out of.  I’m  so glad i found this post. Me and my ex were together for just two years, lived together and now we are both back at parents (i am 24 hes 23).  
    He has nice friends, and he is a nice person but it was just one friend, and his sister. His sister fancies my ex (but she has fancied every other on of her brothers friends so that not  surprising). The last 8 months of our relationship was an absolute living nightmare. The friend (who is the the “ringleader” in my eyes) and his sister took an instant dislike to me, i think its because my  boyfriend  was always the single one, always readily  available  to go out and have drinks whenever anyone wanted   – then he met me and it all changed. So i think they disliked that.

    Anyway, this friend was having a BBQ to celebrate his younger brothers birthday and i got invited (i thought that would be too goo to be true) the week leading up to it, my ex boyfriends so called friend ignored all calls and text from him assuming it was a bid to stop me from going. My ex was annoyed at this and hurt but as men do, they put it to one side and still be friends. They all go out as couples but we was never invited, this friend uses my boyfriend for a place to stay after a night out, money, lifts to places and non of it is  reciprocated. This friend drink drives, cheats on his girlfriend. The funny part is when i am around he is so nice to me telling me how much he likes me – he is such a patronising little ****!  

    Another time we was out in town, and i was at the bar, it was busy and some bloke has his elbow near mine, this friend began to have cross  words  with this fella because he thought he was elbowing me. The bloke at the bar the became a bit angry at this friend and do u know what he did????? He, the friend, turned around and let everyone else get him out of the situation and probably stopped him from being in a fight!! What an absolute dick!!!!  

    It took its toll on me, i tried to tell my boyfriend how much it was upsetting me, after a million buckets of tears and stuff i just felt like he  didn’t  have my back and i  wasn’t  supported. So i did the same as the original poster, i   decided to follow my gut, end the relationship and see who he chose. Its been 3 months now and we have had contact, seen each  other  now and again, but recently my ex has decided its best to not speak anymore because i  dunno  he has his own reasons.

    I’m  so sad, im so angry and im so hurt. I cant understand why anyone would chose to go from   having their own flat, and cat and holiday booked to america next year to being used by a friend and pissing all their money up the wall.  

    I’m  finding this no contact thing really hard, really hard. But now i have to accept he has  blatantly  chosen his friends and the single lifestyle over me 🙁
    It  hurts  so bad……I  don’t  know what else to do now but give up.

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