I have a dear friend that I’ve been close with since college. We’ve been by each others sides through many happy, sad, and life changing experiences. I was there through the death of her father. She stood by my side when I got married. My friend has a generous heart, a hearty laugh, and is one of the few people who I know I can turn to if ever in need.

So here’s the complicated part, since we’ve been friends, my friend has had a habit of consistently letting toxic people and relationships into her life and clinging to them for long periods of time. When we were college roommates I didn’t notice it as much because I was young and had a lot of my own things going on. However, once college ended and we started forging our careers and shared an apartment together, I noticed that she was still making some of the bad choices one is “supposed” to grow out of- consistent binge drinking, clinging to toxic loves, etc. For a while I rationalized it as her being young at heart and perhaps she was still learning her limits. Who was I to judge how another person lets off steam? However, I knew something was wrong when she came to me with a big secret. She had been getting romantically involved with a family friend who was in a committed relationship and had children. What made things worse is that she was close friends to the man’s girlfriend and frequently babysat their children. I was also a friend of this couple and felt very awkward about what was going on. My friend seemed so over the moon with her new love, and I wanted to so badly to be happy for her, but I couldn’t. I knew that she was playing with fire. I was so confused. How could my dear, sweet friend be involved in such a bad situation? How could she do this to her friend, to their kids and to herself? I didn’t understand how she got into this situation.

Finally, one day when my friend was talking to me about her feelings, I had to let it out. I let her know that I wanted to be happy for her, but couldn’t given the circumstances. I told her I was worried about what this could do to the man’s family, and that she deserved to be in a “clean” relationship free of hiding, scandals, and lies. I suggested that if their love was real, then perhaps things could wait until he properly ended his current relationship. I tried to be sympathetic to her feelings, and she seemed receptive to my opinion. Within days, their relationship was discovered by the man’s girlfriend and proverbial s*** hit the fan. The family was devastated. The man chose to stay with his girlfriend. My friend was ostracized by her second family. She was crushed.

This seemed to trigger a tidal wave of troubled relationships. Dating coworkers and then cheating on them with other coworkers. My friend, who came out of the closet about a year later, started going after single straight women, straight women in relationships, bosses, pretty much anybody that would almost certainly not reciprocate her love. At first she said that it was the thrill of “getting them” that motivated her, but then she would fall hard and end up getting her heart broken. Again, I tried to take a step back and be there for her when the pieces inevitably fell, but it started getting harder and harder to do.

An eclipsing moment would be when she dated a coworker of mine and hid it from me for almost a year. During that time, my coworker was dating a few other people at a time when my friend thought they were exclusive. When she eventually told me about the relationship it was only after I happened to mention meeting my coworker’s new boyfriend. My friend’s face sank and she confessed her relationship. My friend’s heart was being broken and I had no clue. I was furious at my coworker and at my friend. How silly and gullible I felt. I was angry about being lied to for a year. I felt slighted by my coworker introducing me to her dates when she was secretly dating my friend. I felt completely at fault because my friend met my coworker through me. “If I only I hadn’t invited her out for drinks,” I would think, “perhaps none of this would have ever happened?” This damaged our friendship. Intentionally lying and hiding something like this from me for over a year was a betrayal. Somehow I managed to forgive her and move past it, but I never forgot what happened.

Now we are in our thirties and this pattern is still happening. She has dated her current girlfriend off and on for over a year. Their relationship is fraught with emotional manipulation and has erupted into a physical altercation on one occasion. She readily admits that this woman is just someone to pass the time with and she has no intentions of settling down with her, but she stays. During one of their breaks, my friend started getting romantically involved with a friend of mine’s cousin who was, and is still, married. I saw the two of them in a picture one day and asked if they were dating. My friend looked at me like I was crazy and said no, they were just friends. I believed her and that was that. I found out about their romance months later, when another friend let it slip. I was heartbroken. Again, my friend was hiding from me. Again, she was getting involved with women who were emotionally unavailable. Again, she was diving heart first into an impossible love. My friend has no idea that I know about this most recent love affair, and I don’t feel like I am in a position to say anything. I hate seeing her go down this path yet again.

I love my friend like a sister. I want the world for her and it hurts me that she settles for so much less than she’s worth. As I try to move forward with positivity and love in my life, it’s getting harder and harder to excuse her behavior with “but she has a good heart!” and , “you know how she is…”. I don’t want to keep inviting drama into my life, but I don’t want to lose my friend. I have even begun to not invite new people around when she and I hang out to avoid her trying to pursue my other friends. I’m at a point that I feel I may have to end our friendship if she doesn’t change her ways. I realize that I am judging my friend, and I do not feel good about it, but I can’t pretend I am okay with her choices. I can see why she doesn’t share these affairs with me, because she knows I won’t be okay with it, but then why continue the friendship with me if she has to lie? I’m at an impasse and am not sure which direction to take. I don’t want to lose her as a friend, but I am also no longer okay with the drama. What do I do?