Do I Suck at Relationships?

Maybe I’m just not willing to settle.

This afternoon, I broke up with my “perfect-on-paper” boyfriend. We had been dating for eight months, and for a while, it was all going swimmingly.

When we met in real life (IRL!) at a local restaurant, it felt like I had “won” the dating lottery. Unlike most of my other former partners, he also lives in upstate New York full time. No more back and forth from Woodstock to the city, schlepping the eternal overnight bag. He is generous, emotionally available, and could hold his own when we jokingly sparred over stupid shit.

So what was wrong with me? Why wasn’t I more satisfied? 

The day before I ended things, I did what I’m assuming most women would do: I vetted this decision with some pals who knew us as a couple. All of them (a married friend, another who is happily dating, and a few of my gay besties) said a variation of the same thing: “Doll, you’ve been feeling this for some time now. You’re not in love with him. He’s a darling man but he doesn’t ‘get’ you.”

I’m realizing that this last part—the “getting” part—is what kept snagging my heart like a nail on a sweater for the better part of a month now. I’d indeed been feeling like he didn’t get me, and more importantly, I wasn’t sure I wanted to endeavor to make him get me. But at this age, does a solid comfortable relationship where there is plenty of common ground, care, and respect make up for that? 

When I started to have the feeling that something was off, I first thought, maybe I’m just bad at relationships; it’s a deeper thing and I’m a self-sabotaging lunatic. I wondered if it is leftover arrested development rebellion from dating sexy dipshits for years. It’s not lost on me that my boyfriend and my ex-husband resemble each other in many ways, and that I left that marriage with a sweet man because I no longer felt vibrant in it. 

So I thought perhaps I could work out what was making me feel less than satisfied if I spent more time appreciating all the things that this relationship does do for me. Maybe I was just overlooking the good and fucking things up with a set of wants that mirrored what I desired in my younger, single years: super hot sexual chemistry and at least some curiosity in offbeat culture (the weirder the better; I have loved some real freaks). But isn’t needing to do the pro/con list a sign that it’s the wrong relationship? The more I thought about it, the more I realized those same wants still carry a lot of weight for me today.

My boyfriend and I had just gotten too comfortable, too quickly. Last week, I not-so-nicely informed him that I thought it was presumptuous of him to leave his clothes in my hamper, and he heard me, because after our eternal lazing around between Christmas and New Year’s Day, he took his dirties home with him. 

I also told him that we needed to revisit the earlier days of dating when he was “courting” me (am I Scarlett Fucking O’Hara?). This meant that for every night when we just melted into the sofa here at my house (where we defaulted to staying because of my pup) with a plate of food that I whipped up for us, I wanted him to reciprocate by taking me out on a well-planned, sexy, imaginative date. I actually said that. And he actually said, “yes, I want to,” and I’m sure was trying his best to deliver. He is, after all, a pretty terrific boyfriend.

How then to explain this tape that seemed to be playing on a never-ending loop in my head? The feeling that this just wasn’t enough. Was it that after a lifetime of partners and spouses, I’m just over the idea of any compromise? 

It’s true that I love my alone time, now that I have it. Being solo in midlife is pretty golden (not Golden Girls, just shiny and bright): I’m finally devoting some of my downtime to the projects I’ve been chewing on for years, including writing a book, deepening my study of tarot, and playing the drums.

When you’re no longer young, but not quite old, it’s also a time of incredible exploration for those who have the inclination (and freedom) to shake things up and look around a bit. You might end up with a whole mess of new tattoos or start eating pussy (oh honey, been there, done that). The ability to simply go wherever the wind blows is intoxicating, and I’ve been blown around enough to know that some of my happiest times have been when I literally did not know where the day would take me. As long as I have a dog sitter at my disposal, I can take off with not much more than a toothbrush and a pair of sneakers in my bag. I’m also old enough to know that this period in my life, when I’m able to bounce around so effortlessly, is finite. Sooner or later, the back, the hips, the knees, the caffeine or dairy sensitivity, will kick in. But right now, I love that I get to be the sole decision-maker regarding how much time I spend flitting around outside the house, and likewise, how much time I spend recharging at home. 

I don’t want to imply that he was a stick in the mud, or that we never went out, but my ex was vastly more interested in the cozy, cocooning side of midlife. And to address the elephant in the room, it can be a lot less lonely when you have someone to do that with. When single in midlife, most people immediately point to the same number-one challenge: loneliness. 

Being in a room full of partnered people can feel debilitating if you’re alone, as you watch those couples exchange the inside jokes that come from decades of togetherness. I know a half-dozen pals (both men and women) who are also dating in midlife, and who have pragmatically said that their relationships are nice enough, but what keeps them engaged is the fact that without those very same relationships on which they are not entirely sold, life might get lonely. I hear that, and I’m sure at some point I will miss the easy comfortability that comes from watching a movie in my pajamas with someone who knows I like ice in my seltzer when he goes to the fridge to get a glass for himself.

I enjoyed those times with him, and hurting someone sweet and kind feels like crap. I did not intend to summon him to my house with a text that read, “I think we should talk. We don’t want the same things.” Normally I would never send this sort of message, and only bring this up in person, but his earlier text about how he was coming to my place to chill for the afternoon set me on edge. I wanted to give him a heads up that “chill” was not on my agenda. 

With all the early 2025 terrors we’ve all been experiencing, and as we look down the barrel at the truly apocalyptic times hurtling towards us as January 20^th draws near, you’d think I’d be reaching out for someone stable, who has my back and looks good on paper. Guess what? I am doing that. I’ve already met the person who I am sure will be a great life partner: me. 

When he arrived at my house and saw my face, assessed my body language, and eyed the blue IKEA bag in which I had gathered up his stuff, he said he assumed there was nothing we could talk about. No, there was nothing to talk about. I wasn’t feeling excited, I wasn’t feeling indulged. That has nothing to do with the younger me and her wants. This is me today.

As a freshly single woman intent on tromping through the wilds of midlife, well-therapized, and still learning more about all her foibles, I believe love can be on the menu, but only if it makes more than just sense. As for feeling “seen,” I can indeed look in the bathroom mirror and I say to myself, “You’re the best thing that’s ever happened to you.” Maybe I don’t suck at relationships; I suck at settling.

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