Hi everyone. I've been going around different forums wondering what I should do, and thought this would be a nice place.

We've been dating for a year, and have been friends for a lot longer. Overall, we've had a great relationship... except for this one guy. Her male best friend, we'll call Josh. Sarah, my girlfriend, and Josh have been friends for a while, best friends, even. I was perfectly fine with it until I found out that in college, they had been intimate a few times. Ok, it's in her past, and I appreciate her telling me. Actually, they'd been intimate, while he was in a relationship. This makes me question her character, but again, I swallowed it seeing as she was honest with me, and it was in the past.

Now, they talk a few times a week, just random chatting online + texting + calling. No big deal. Until recently, she was asked to go ring shopping with him... for his girlfriend... who he cheated on... with my girlfriend.

I talked to her about this, and told her that this is VERY wrong, and for the first time in our relationship, I told her that she shouldn't do this. We had a long talk about this, about how he seems completely not guilty about the fact he's cheated on his girlfriend a few times. That night, I flat out told her that I didn't like him as a person.

Two weeks ago, he's been texting her a lot more often, at random times throughout the night, and once I picked up the phone (she told me to while she was in the bathroom), and he didn't call/text anymore that week. A few days ago, my girlfriend and he had a long chat about how she's slowly distancing herself from him, simply because of the fact that he is going to propose to his girlfriend, and due to their past, she should reestablish a boundary and move forward with him as a friend, and leave the past where it is. She told him that it was wrong for him to ask her to go ring shopping with him, considering their history, and his response was, "Yeah, but she'll never find out.."

I appreciated what she did, to set some sort of a boundary with him, but his response to her just recently was, "I know you said that you wanted some distance, but I'm going to make that extra hard for you."

Also, he said, "You were the best thing about college."

Now, this has left Sarah and me in a weird state, because I'm not happy about this guy, but I'm never going to tell her who her friends should be. Also, she seems to be handling this situation well, (she seems to be at least trying to make up for what she did in the past). She can sense that I'm unhappy, but she's not sure what she can do.

We left the conversation in a quasi-annoyed state, because I'm unhappy, and her response is, "I'm doing what I can, what more can I do?"

To make a long story short, girlfriend and her male best friend had been intimate in the past, male best friend cheating on his girlfriend with my girlfriend. She wants to set boundaries, but he won't listen.

You say you're never going to make demands on who her friends should be, but you have done just that.

It seems like your involvement in their friendship, has brought up the past relationship they had together. I think you put yourself far too much into her life, and have caused problems.

She is your girlfriend. If you cannot get past her past, or insist on discussions about what is appropriate or not appropriate in her relationship with her friend (i.e. ring shopping), perhaps you should move on.

You have put her on the spot. Lose a friendship, or, lose you. You won't be able to accept him in her life, as you have already judged him and told her you do not like him. What gives you the right to dictate who her friends are.

If you don't like her friend, and it bothers you that she has a past, with intimacy with him, and even though he's getting married, you are very bothered by this- right down to establishing boundaries for her friend, you should move on.

Jealousy is rearing it's ugly head, and there is no other way to see it.

You say you're never going to make demands on who her friends should be, but you have done just that.

It seems like your involvement in their friendship, has brought up the past relationship they had together. I think you put yourself far too much into her life, and have caused problems.

She is your girlfriend. If you cannot get past her past, or insist on discussions about what is appropriate or not appropriate in her relationship with her friend (i.e. ring shopping), perhaps you should move on.

You have put her on the spot. Lose a friendship, or, lose you. You won't be able to accept him in her life, as you have already judged him and told her you do not like him. What gives you the right to dictate who her friends are.

If you don't like her friend, and it bothers you that she has a past, with intimacy with him, and even though he's getting married, you are very bothered by this- right down to establishing boundaries for her friend, you should move on.

Jealousy is rearing it's ugly head, and there is no other way to see it.


Drat, I was really hoping that wasn't the answer. Is there a way to fix this? Or is it at that point where I have to move on? I really don't like that it's come to this. I was never a jealous person. It's just when this guy from her past is coming onto my girlfriend, when HE HAS A GIRLFRIEND, and she makes excuses for him, "Oh, he's just kidding," or "It's just the way he is," it really bothers me.

IF this friend of hers is a scumbag as you say, and as he very well could be, the point is that you pushing the issue, puts you on the same level as him.

That is why this will reach a point where she will have to choose.

You are far better to not discourage, or encourage, her to have contact with him. We have all had friends that to others were less than stellar, or they were users, or scumbags as you put it, but we were blind to it.

It will have to be her decision, without your intervention. If you can see the bigger picture here, you will gain far more than what you could potentially lose.

I think that if you keep your own personal feelings about this guy in check, and give her enough room to show that you trust her, she will hopefully limit contact and communication with this guy, on her own.

I think I would totally let her handle her scumbag friend on her own, but where she was honest, so should you be. Establishing the boundaries of good behavior is essential between couples, and suspicious behavior is unacceptable as in calling and hanging up. Any of her friends (or yours) that cannot honor those boundaries is unacceptable.

This fellow may well think he can go behind his girls back, but she shouldn't expect YOU to go along with him thinking its okay for HER to go behind yours. She has not, but her process of dealing with this friend has to be one of respect and until she sees him as the disrespectful scumbag he is, then all you have is trust and honesty to guide you through honest communications.

Just me, I would never even allow any of my wife's friends (or mine) define the rules of good behavior between us man, or woman and certainly not an ex, willing to cheat with my girl. He can't show you proper respect when calling, then maybe you have to let her know that you will not accept that kind of disrespect at all. That's not jealousy that's respect, and it starts between the two of you to move forward in a positive healthy way.

If you cannot move forward together, then you damn sure can move forward apart.

I agree with talaniman, your girlfriend has to find the boundary with this guy. You have to distinguish your boundary of jealousy vs being disrespected. Are you in fact not making friend choices for your girlfriend and just asking for respect?

My wife is good friends with a old girlfriend, but the old girlfriend and I have set firm boundries. And that is what they need to do.