The Jealousy Monster in the Age of Cuffing Season

My friend met someone at karaoke the other night. I, feeling under the weather, stayed home and watched a show I didn’t even enjoy. Apparently, this guy sang “Under the Bridge,” my friend’s karaoke go-to, and they ended up chatting for ages about stately homes, particularly one in West London with beautiful tiles. As she was sharing her number, he blurted out, “I’ve got an Art Pass, and I’m not afraid to use it!” It was, of course, a cheesy pickup line, but the whole story made me feel a little…uncomfortable.

I pretended to be thrilled for my friend, gushing on the group chat. But inside, a small, green monster was stirring. I found myself scrolling through Instagram, trying to distract myself from the creeping jealousy. What if I had gone to karaoke that night? Would I have met him? Would he have liked me? Or would I have been awkward, insecure, and ultimately, just not his type? Why was I even thinking this way? It was ridiculous, I know. My friend is amazing; he’d probably be drawn to her anyway. And I barely knew him! Still, the little monster insisted on playing its game.

The next morning, my friend was already worried. He hadn’t responded to her text. This, despite saying he had a great time and wanting to do something together. This, despite texting her later that night with a picture of his cheesy toast. I felt myself getting frustrated. Here I was, single for five years, constantly running away from connection, and she was fretting over a guy who hadn’t even had the decency to send a simple “good morning.” I wanted to talk about my own dating struggles, my own insecurities, but I held back. It felt too raw, too vulnerable. There’s a part of me, a part that I hide even from my closest friends, that feels ugly.

Being single is tough. You need allies. It helps to remember all the amazing single women I know, the kind, funny, interesting people who are the best part of my life. But the fear of being left behind is real. We joke about never getting boyfriends, but there’s a genuine longing in those words. There’s a societal pressure too, the idea that women are competing for limited options. And to be honest, sometimes it feels that way. There’s always one decent guy at a party, and he’s probably not over his ex.

It’s easy to fall into the trap of comparison. But it’s dangerous. Just like the yoga teacher says, we lose our balance when we focus on what others are doing. We become insecure, go out for the wrong reasons, and end up projecting that stress onto others. Then we come home disappointed, wondering why we’re still alone. People tell you to stop expecting to meet someone, but the truth is, we’re always expecting, always hoping. That’s what cuffing season does, amplifies the pressure, the longing.

I crave the simple things, the kind of closeness that comes with a shared horror film, the comfort of Sunday mornings reading in bed together, a warm pub with a glass of red wine. I want that intimacy, that connection. And yet, here I am, feeling a tiny bit of relief that the guy from karaoke hasn’t gotten back to my friend. It’s a ridiculous, contradictory emotion. Maybe he’s just not ready for a relationship. Maybe he’s going through something. And even though I want to be happy for my friend, a little voice whispers, “See, maybe it’s better this way.” The jealousy monster is quiet now, but I know it’s still there, lurking in the shadows, waiting for the next opportunity to rear its ugly head.

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