Help! My Childhood Best Friend Keeps Stalking Me for Attention. I’m Considering Drastic Measures.

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I grew up in a rural Midwestern town, but moved to the nearest large city as an adult, a little over a decade ago. Throughout my childhood and adolescence, my closest friend was “Kate.” We kept in touch throughout college but drifted apart a bit afterwards. Kate stayed in our hometown after I moved away. Long story short, I abruptly cut Kate out of my life several years ago after she made a racist comment to the person I was dating at the time (Kate and I are both white, my ex was not).

Two or three years after this happened, Kate reached out to say she really needed my support. Her dad had died and she was struggling with her grief. She also gave a very half-assed apology about her behavior towards my ex, who I was no longer with. I knew Kate’s dad, so expressed my condolences and listened while she talked and vented, but didn’t make any grand overtures towards reconciling our friendship. She also never fully owned up to the racism.

In the years since, she has reached out periodically, usually with a dramatic story about her current situation (being fired due to “accusations” of using drugs at work, emergence of a mysterious chronic illness, alcohol use issues, tales of her neighbors making threats against her, etc). If I don’t answer her phone calls or if I tell her I’m unavailable to chat, she continues to reach out in other ways such as sending messages on other platforms, sharing a bunch of Instagram posts in a row, or commenting on my social media posts. She has even called my mom a few times, because my mom will always pick up and listen, even though my mom has expressed to me that this makes her uncomfortable.

Here’s the thing: I really do sympathize with Kate. In my early 20s, I dealt with several years of my own untreated mental illness, substance abuse, reckless decision-making, and self-inflicted interpersonal drama. But now I’m in my 30s and after many years of therapy, my life has stabilized. I’m married and have a great job, just purchased a home, and am six months pregnant with my first child. And at this point, I really just … don’t want to talk to Kate. I don’t want to invite drama into my life when I spent years undoing the consequences of my own drama. And I know from both my personal experiences and from the last few years of sporadic contact with Kate that no advice or sympathy will influence her to make choices to improve her own life. Is this callous of me? If so, how can I provide support while still maintaining my own boundaries? Or, is it okay for me to no longer maintain any kind of relationship with Kate? And if so, should I tell her this directly?

— With Friends Like These

Jenée Desmond-Harris: I’m going to come clean. I did it again. I pulled this letter from the inbox after giving it a quick glance, seeing that it was long and looked kind of juicy, with the friendship breakup and racism and mental illness and everything. But now that I’ve read it closely, there’s actually not much to say. Yes, it’s totally okay to no longer maintain any kind of relationship with Kate! And I think the right thing to do is to tell her, without expecting her to take it well. Is that right or is this more complicated than that?

Lizzie O’Leary: I also think the right thing to do is tell her. Look, there may be some mental illness there, and the LW may have some residual sympathy for Kate. But if the LW is asking for the right thing to do here, it is absolutely okay to just end this relationship. I am a super direct person, and if I were the friend dumpee, I think I would rather be told “this isn’t working for me, for my own peace (or whatever), I don’t want to be in contact.” It sucks, but it’s clear. And based on what the LW is saying about Kate, it actually sounds like a slow fade/ghosting will not actually get through to her. BUT! I know that not everyone feels that way. LW, I give you permission to drop the hammer. Jenée, does this hammer need a velvet glove?

Jenée: Well, speaking for the Very Avoidant and Afraid of Hurting Anyone’s Feelings community, I would probably make it a little softer. Normally, I don’t care about being gentle when it comes to racists or other people who are actively unkind to others. (My good friend in college used to joke that while I was mostly extremely nice, certain people brought out—pardon the outdated expression—”Keepin’ It Real Jenee,” my alter ego who would not hesitate to eviscerate someone.) But the mental illness piece here is making me want to use a little bit of a velvet glove for Kate.

I’d probably do something like this: “Hey, I know I’ve been hard to track down lately and not responding to a lot of your messages. I have to be honest and tell you that your failure to own up to your racist comments is hard for me to get over and has made me feel a lot less close to you. I also think we don’t connect as well as we used to in general. I wish you the best but I’m not up for being in contact at this time.”

Tell me what you think about that? But I also want to make another point while I’m thinking about it, and it’s one that applies broadly to ending friendships that aren’t working: Life is busy! If you work a job and need some time to get ready for that job and maybe clean your house and handle life admin, you have like three free hours a day at best. Throw in a kid, which this LW will have soon, and it’s even less. Also, there are a lot of really kind, great people in the world, and many of us struggle to find time to really be there for and connect with loved ones who we think are amazing. That’s the context I’m thinking of when I urge people to end relationships that aren’t working. You have a non-racist, fun, thoughtful friend who could use the energy that would otherwise go to Kate! Or a grandma who would love a phone call. Or a person you met through work who seems amazing and wants to get coffee. A person doesn’t have to be a monster for you to decide you want to allocate your time and energy in a way that doesn’t include them because others will add more to your life.

Lizzie: No, I think you are absolutely right. This is why I have an editor, lol. I mean, I wasn’t saying we should take my message verbatim. That would be awful! I was just going for sort of a gist of things vibe. But yours is way better. And I absolutely agree that life, as we are reminded more every day now, is incredibly precious and fleeting. We should spend the brief time we have here with the people and projects that truly matter to us. One thing I have noticed in a lot of our uncensored letters lately is a lot of people wrestling with how to set and hold a boundary without feeling “mean.” And, I don’t want to be overly presumptuous, but a lot of them are women. I think we are not socialized to say no. And if we DO say no, we feel like we are doing something harsh or impolite. This is all made more complicated because I think there is a bit of a trend of social media encouraging cutting off contact, or enforcing draconian boundaries. So it can be hard to find a middle ground that is both kind and empathetic to oneself, and also communicates what you are actually willing to spend time on, or not.

Jenée: Yes, yes, yes to all of his. Also, it’s not mean or unkind to have the kind of relationship you would have had with someone before technology made Instagram DMs and texts easy to fire off. Who are the people who you would still be in contact with using only 1990 tools? Who would you be friends with if you had to wait for their call at home and then call them back and make plans to see each other at a certain time? All the other people aren’t really friends—they’re people who were once in your life who happen to still have a kind of access to you that is out of sync with your closeness. I don’t think we were built to be responsible for categorizing and maintaining and stressing over so many relationships.

Lizzie: That is absolutely one of the darker sides of social media. It can be lovely to learn that the person who held your hair as you barfed at the spring formal has been promoted, but you can’t feel beholden to that. LW, we see you. Focus on the family you are building, and the life you want to have.