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?

Valerie

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….

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