How Do You Know When It’s Time to Break Up With a Friend?

The writer was put off by a close friend's penchant for having extramarital affairs—with other married men. Is it wrong to part ways with someone whose values clash with your own?

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Breaking up with a boyfriend is hard. But, breaking up with a girlfriend is even harder. I’ll admit it, when it comes to female friends I’ve had a lot of break-ups. I have not always made the best choices. I’ve found myself besties with the frenemy who copied my every move while trashing me behind my back, the super fan of my ex-husband, and the plus-one party pals who are quick to say yes to a glamorous event but not there for you when you need them.

This is why, as I get older, I think long and hard before parting ways with yet another friend (and consult a therapist about it!). At the same time, as I grow emotionally wiser, I find myself caring more about the quality of people I have around me. I used to bond over silly things like fashion, music, and which Kardashian to hate the most. Today, I feel a strong pull to surround myself with women I respect on a deeper level. Women who I’m proud to call my friend. Women who share the same morals and values as I do.          

Not women like Cynthia*, a married mother of two who cheated on her husband and has a two-decade history of having affairs with married men. She’s been with her “boyfriend,” Robert*, for a year now—he is married with two children. While seeing him, she had a handful of other affairs with married men she found on Tinder, Facebook, or at bars. And, she didn’t always use protection and she put herself in dangerous situations by meeting up with strangers at hotels that she paid for, well, that her husband paid for unknowingly because Cynthia doesn’t earn a living.

I first met Cynthia nearly 20 years ago, and at the time she was sleeping with a married man at work. We parted ways when her emotional chaos was consuming our friendship. We had many conversations about why she’s marrying a man she isn’t sure she loves or is even attracted to. When we reconnected this past year after a 15-year hiatus, I thought she changed. I was wrong.

She slowly started confiding in me about her cheating ways and alternating between regaling with me with her sexual escapades and spazzing out to me because her one-night stand from Tinder didn’t text her back. She even asked to use me as an alibi, which is appalling seeing that she knows I broke up with husband over myriad of things, but one of which was his cheating. (My Husband Convinced Me I Was Insane.)

I was disgusted by her behavior, especially as someone who has never cheated on a man and holds fidelity in high regard. But I felt bad “dumping” her again. I dumped her once over her emotional recklessness. Here I am again faced with the same issue. But this time, I tried hard to find a way to be understanding and help her. I thought maybe she was just going through a phase. I felt like I was being judgmental if I dumped her again. At the same time, I felt bad for her. I recognized this is a woman with very deep-seeded emotional problems who needs help.

After a year of trying to point her in the right direction, I finally hit my breaking point.

“I find you morally reprehensible!” I screamed. “Stop calling yourself a feminist! I do not respect you and I cannot be your friend. Get help!” This is the harshest thing I’ve ever said to another person, let alone a friend. A good friend.

Yes, there was a better way to express this and I am disappointed in myself for being so cruel. But, I am more disappointed in myself for not standing by my convictions and staying friends with a person that I don’t respect.

What’s it to me? Why should I care what my friend does in her private life? I needed to separate myself from toxic people—it’s that simple. “It is an emotionally healthy thing to do,” says psychotherapist Dr. Jenn Mann, host of VH1’s Couples Therapy With Dr. Jenn. “If you are morally and ethically opposed deep to the core about what your friend is doing, it might be wise to cut way. By choosing to not be friends with her you are being consistent with your own values and what you stand for.”

Licensed marriage and family therapist Ana Santaolalla agrees. “If you find yourself constantly on your friend about what you think she is doing wrong, it’s really not good for either person,” she says.

It seems like a simple answer in hindsight, but in the midst of it all it was quite challenging because I felt great compassion and sympathy for her, as I knew she needed psychological help.

“Women who have a history this tend to be women who like the unavailable man, and who are very incapable of emotional intimacy themselves so they seek out people who can’t show up emotionally and who won’t demand that of them,” says Dr. Mann. “They also tend to be women who on some level feel very bad about themselves because what you’re doing is you are choosing to be in second position and that is a reflection of how you feel internally and what you believe your value is.”

Dr. Mann explains that often times women who seek out married men have specific issues in childhood that get them to this point. “In general, it can be an unavailable father, or addiction or chaos in the home, emotional issues like depression and personality disorders, or if a father sexualized her by focusing too much on her appearance, which could give her that idea that that is where her worth lies. She might also have self-esteem issued based on where she’s at in her life in terms of career or other things that she might think she’s not doing as well as she’d like,” she explains.

I also felt—and still feel—empathetic toward her because I recognized signs of love and sex addiction in her behavior through my own experience (I Am a Recovered Love Addict). “Usually people who engage in sex with multiple partners, unsafe sex, risky behavior, and/or relationships with married men can be signs of love or sex addiction,” says Santaolalla. An anonymous SLAA member echoes that – “You hear stories like hers in meetings all the time and she seems like someone who could benefit from looking into this pattern further.”

I ran some of the signs of sex and love addiction by Cynthia and she told me, “I know. Yes. I know.’ She said she related more to the love addict side than sex, which makes sense because she admitted to not being able to orgasm. The sex just helps her feel wanted.

The biggest problem is that she doesn’t think she’s doing anything wrong. She justified the affairs by saying things like, “Well, the wife is a bitch.” “They might not be divorcing but that marriage is over.” “The wife doesn’t even want sex.” Cynthia felt no guilt or remorse, and showed no signs of stopping.

Santaolalla and Mann both say that the lack of remorse can be a sign of someone with an anti-social behavior disorder or narcissistic personality disorder. “Certainly a lack of sensitivity and inability to have empathy for others, the lack of remorse, are a few of the character traits of an anti-social personality disorder, but this doesn’t make her that. This is one symptom of that,” explains Dr. Mann.

“If she’s not willing to change,” continues Dr. Mann, “it’s a wise choice for you so you don’t have to sit through 10 more rounds of her fucking someone else’s husband. This should offend any woman and you don’t have to be cheated on for it to be a hot topic. It is counter to the bonds of sisterhood and feminism.”

If you are contemplating breaking up with a girlfriend, ask yourself these five questions:

1.     As they say, birds of a feather flock together. Do you want to be defined by your friend’s behavior?

2.     Are you proud to call her your friend?

3.     Are her morals and values consistent with your own?

4.     Does she bring more calm than chaos to your life?

5.     Do you respect her?


If the answers are “no,” then your choice is clear. But, instead of screaming at her like I did, try a more delicate route.

“It’s best to talk to them first and be radically honest,” says Santaolalla. “Instead of pointing the finger at her, use ‘I’ statements. In this case, you could’ve said, ‘When you tell me about your affairs, I feel uncomfortable and feel I can’t relate or connect with you.’ It’s difficult, but it’s a healthy choice to choose not to be friends with someone who doesn’t reflect the same lifestyle, morals, and values as you.”

As Booker T. Washington said, “Associate yourself with people of good quality, for it is better to be alone than in bad company.”

I couldn’t agree more. I am happy to be free of this woman, but I am sad in knowing that she is still out there wreaking emotional havoc on others and herself.



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