Dear Fuck-Up: How Do I Stop Obsessing Over My Ex?

Dear Fuck-Up: How Do I Stop Obsessing Over My Ex?

Dear Fuck-Up,

I had a rather dysfunctional year-long relationship with a man—let’s call him James—that ended more than two years ago. Among other issues, I felt that I was very in love with him and he just… didn’t love me. I felt like I was always dancing for his attention—trying to be clever and interesting and sexy—and it was such a fucking high when I succeeded. I never really understood why he stayed with me so long, and why he ended it when he did. I was deeply, painfully, obsessively hung up on him for a long time after the relationship ended, but that pain ended up spurring a lot of really positive personal growth (including going to therapy and starting medicating my anxiety) and I’m now in a great place and in a lovely, fulfilling relationship with a man that I plan to spend the rest of my life with.

I genuinely don’t think I’m still in love with James—if he walked into my life tomorrow and told me he wanted to get back together I would say no. My problem is that despite this he still occupies a fair amount of real estate in my head. He has an objectively brilliant, creative, unique mind; he’s the smartest person I’ve ever met and I have always found him utterly fascinating. Everyone else I’ve dated, I feel like I “figured out” after a certain time and they lost some of their luster and became human, but James was so distant and aloof and I never figured him out. It’s like the mystery of him—and my time obsessing over him—carved out a deep channel in my mind that still hasn’t filled back in, and my thoughts still flow into that channel more often than I would like.

How do I care less about someone that I find so fascinating? How can I remove him from the pedestal in my mind?

He has since moved away but I’m still so curious about his life—he has a pretty limited social media presence but I find myself combing it for clues about what he’s up to. I also post things with him in mind—wanting him to be interested in my life and to find me clever and interesting and impressive still—and there’s a little burst of pleasure when I see that he’s seen my Instagram story or whatever and I wonder what he thinks of me. I have dealt with this by repeatedly deactivating my social media. This helps (although I still find myself googling him occasionally) but when I periodically reactivate I’m just right back in that same pattern—the first thing I do is check his page. It’s like I need to poke that wound to see if it still hurts and it mostly doesn’t, but kind of does? I’ve also tried blocking him, but it’s just too easy to unblock occasionally just to “check” (what am I checking?? I don’t know). Perhaps I need to just block him permanently, but I still care about him and am interested in him and I would really like to be able to engage with him in that normal, casual way one interacts with old friends on social media. I’m embarrassed that I still need to regulate my social media interaction with someone who I dated so long ago.

I love my current partner so deeply—this relationship feeds me while my relationship with James was so painful and draining—and it would hurt him to know how often my mind still drifts to James. It feels shameful.

How do I care less about someone that I find so fascinating? How can I remove him from the pedestal in my mind? How do I stop wondering about his life and internal state? Is there any way to have a normal social media interaction without becoming somewhat obsessed every time I get a hint of new information about his life?

I know you’ve answered a lot of questions to this effect, but I would greatly appreciate your help.

Thank you so much,


Dear Stuck,

You’re right that I’ve written about this topic before, but I’m happy to again because I am a little bit obsessed with the idea of obsession. There are personal reasons for this: I’ve mentioned in the past my own failures to get over people who do not want me, and how humiliating I find that state of affairs.

Last time I mentioned how we make fictions of other people—it is small comfort I know, being told you are hung up on a fiction not a person, but no less true for it—though I didn’t really talk about how those fictions can be quite useful. The first writing assignment I ever accepted I took because I thought it might impress someone who rejected me. That perhaps he would see it and if I could make it smart enough or good enough then I would be too. Is that pathetic? Perhaps! But I now mostly manage to pay my bills by writing and it’s certainly not the worst job I’ve ever had. Your obsession has catalyzed positive changes in your life as well, as you rightly note. Seize on motivation where you can find it.

But you should also be clear with yourself that you will never truly fulfill your goal of impressing him because the whole reason you want to is that he found you unimpressive. He is fascinating to you because you could not fascinate him. In this sense, the fiction you have made of this man is casting him as your ultimate judge. I have no doubt he is in some ways very intelligent, but I suspect the reason you think him uniquely brilliant and wise is that you believe he possesses some secret knowledge about your worth: This man does not love you and on some level, you believe him right not to. Hence, his rejection seems more meaningful than your current partner’s acceptance.

There is no mystery to this man, he was simply withholding. How boring! How very tedious to waste one’s time being distant and aloof with those who want to know us. It is natural to want things that other people hide but keep in mind that their inaccessibility alone does not make them valuable. You already have something worth wanting.


A Fuck-Up

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