Friends With An Ex? How To Handle the New (“Toxic”) Girlfriend

Dear 40-Somethings,

A few years back, I moved back to the U.S., and the prospect of dealing with a long distance romance ultimately caused the relationship between my boyfriend and me at the time to fall apart. It ended on fairly good terms, and after a while we were able to navigate the new waters of just being friends. He’s had a few girlfriends and I’ve found (much to my surprise!) that I am genuinely happy to see him being happy.

However, his most recent girlfriend has put some strain on our relationship. She is someone who I knew back when I was abroad, and she was always a bit rude and would often try to tell me that my boyfriend “could do a lot better than me”. To make matters worse, now that the two of them are dating, she’s started to send me messages demanding that I end all contact with him.

Since he’s among my dearest friends, I was upset about this. I eventually mentioned these messages to my ex, who responded by saying “well, she’s allowed to say what she wants”. While he’s tried to maintain our friendship, it makes me uncomfortable knowing that he won’t stand up to his girlfriend in my defense, or allow me to confront her about her behavior (for fear it will ruin their relationship).

I’ve slowly started to withdraw from him, but he’s begged me to reconsider. So my questions are: would you stay friends with someone who has a significant other who is causing problems? Does the fact that a friend is dating a bad egg and allowing bad behavior signify a mistake or problem in their judgment of character? I don’t want to insist that he break up with her but I wish he would at least say he doesn’t condone her behavior. How would you handle the situation?

Dear 20-Something,

I wouldn’t end your friendship only because their significant other is causing problems, but I would re-adjust my expectations and change the level of friendship to be respectful of his current relationship.

His dating a “bad egg” and bad behavior may be more attributed to learning about one’s self rather than a problem of character.  Over time we learn about what type of boundaries make sense and what type of relationships we can handle by being in different types of relationships.  My advice would be to move on – and learn how to re-adjust your friendship.  If he does not take a stand, he is telling you that she is very important to him.  With that said, do not insist that his new relationship is toxic.  Your role as a friend is to simply be supportive.   I would not impose my will – or judgment – on him but rather re-assess the dynamics combined with what you want and can get from this friendship given all that you know. — 40-something, Real Estate, NYC


Dear 20-Something,

I think you already know the answer here and are hoping that people tell you otherwise. 1) If you are such good friends, HE would determine what transpires and she would never think to speak to you that way. 2) If you were really good friends, you would not tolerate such behavior, which leads me to believe you may still have romantic feelings for him. Regardless, for reasons 1 and 2  (or, perhaps, 1 OR 2) – you should curtail the friendship.  You are young, smart and vibrant – if you are meant to be friends with this gent, you can pick up on said friendship years from now when you get something positive out of it, and it will be better!  – 40-something, Marketing Executive, Chicago


Dear 20-Something,

I would try to save the friendship if it is truly not a case of you in fact holding on to a romantic aspiration and wanting more than a friendship.  To have a true guy friend is a good thing if you feel like he adds something to your life more than the toxic girlfriends takes away from your life.  In today’s world women and men are staying single longer or are not marrying at all. So it’s time we shouldn’t have to cut off friendships when your guy mate gets a new gal or gets married.  I would have to say there are guy friends I miss and those I have kept, I truly enjoy.   I think, against the “When Harry Met Sally” message, that you can be friends with the opposite sex.

There are boundaries of course. Rather than having him be the go to guy for all your needs figure out what his friendship means to you and focus on seeing him when those times are true. It’s not your job to confront her on her “toxicity” and behavior.  Her animosity towards you has way more to do with how she feels about herself than it has to do with you. Just ignore it and kill it with kindness.

That said he has to live up to his end of the friendship. If he is not willing to stand up for you in any situation, or at least draw the boundaries with his girlfriend, you have to ask if he is really a friend worth keeping. If he is a true friend hopefully you can talk about this a little more over time. – 40-something, writer, consultant, NYC




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