EDIT: important note!!! I have been too hasty in my past relationships to cut people off when seeing red flags. So I was trying to exercise more benefit of the doubt in this relationship. Is this enough of a red flag to be questioning the larger relationship, or is this a workable issue?

My boyfriend Craig [27M] and I have been together for six months. He has a best friend Emily [27F]. Emily and I get along great—this post isn’t about her.

Craig and Emily have a third friend Teresa [28F].

Craig and Emily have nothing nice to say about Teresa. Every time they mention Teresa, it is because Teresa has been selfish or rude or otherwise inconsiderate. From being intentionally cruel to men, to nonstop complaining about her—quite charmed, I’m told; she’s very wealthy—life, to picking fights with Craig and Emily when they attempt to point out the bad behaviour. They have verbatim called her a terrible person when they talk to me, though perhaps they were exaggerating for effect.

The only reason I’m given for their continued interaction is “she’s our friend.” I have only interacted with her once. She didn’t seem to want to talk so I left it at that.

All of this has made me dread hanging out with her!

Now, Craig is asking me to go on an all-day hiking trip with Teresa and Teresa’s friend. Emily can’t come. I told him honestly I’m hesitant to go spend the day with his friend, because all I’ve heard about her is bad. He got upset with me, saying the fact he chooses to be friends with her should be enough for me to have faith that the hike will go well.

Is it normal to speak so poorly of friends?

I don’t speak about my own friends like this ever, so I don’t know if it’s a me thing or a him thing.

What should I do to alleviate my feelings of unease? I have asked him to say nicer things about her, but that seems to upset him as well.

4 comments
  1. She might actually be a nice person. They are her “friends” but it doesn’t mean Craig and Emily are nice people to everyone. They obviously hang out with this person, and that doesn’t exclude them from being gossipy jerks too. If she’s wealthy or sets firm boundaries with men, some people perceive her as being a privileged brat who should be “nicer” to men.

    You know they’re crappy friends to her. You can see it.

  2. It is never normal to speak badly about someone you call a friend, much less ALL you have to say about them be bad. I wouldn’t go, the first time you met her she didn’t even wanna talk, she most likely wont during the hike. Even if she does talk to you? I get a feeling it wont be something nice and cuddly that comes out of her mouth. Craig shouldn’t be making you feel bad about saying no to hang out with someone that 1. You’re uncomfortable with 2. He himself has said is a HORRIBLE person. That is a red flag, he should respect your boundaries.

  3. It’s odd that you don’t judge his actions and character but only Teresa’s from his words.

    He does this behaviour and still calls them friends.

    Maybe you should go and observe everyone. Use it to decide if you really know your BF or see him as you wished.

  4. Tell him you honestly don’t understand why he’s friends with someone he’s called a terrible person, so either he’s admitting you shouldn’t trust what he says, or his insistence on keeping Teresa in his life despite her apparent lack of redeeming qualities is his problem and you don’t want to get dragged into it. At the very least, he should ask himself whether it’s really in his best interest for you and Teresa to spend time together in case she wants to know what he’s told you about her. (And seriously, you should ask yourself why you’re with someone who talks about their supposed friends like this behind their backs, because who knows what he’s saying about you?)

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