Is being an (actually) hopeless romantic the best way to find love this Valentine’s Day?

When I started writing this column a year ago, I’d never told anyone I loved them. Which was fine for editorial purposes, because this is a sex and dating column. I wanted love from people who kept me at arm’s length. I thought if love was hard won, it would last. That if love was universally acknowledged as rare because it was coming from someone who didn’t offer it readily, that it would be less likely to fade or disappear. 

Rare love as some sort of karmic reward was something I held out hope for and slowly gave up on. I was disappointed and blindsided over and over again. Friends, acquaintances, and coworkers were surprised to hear I’d never officially been in a relationship (yes, I am in therapy). You know that time tried, certifiably annoying line of “it happening when you least expect it?”

That is easier said than done. A crush or situationship would fail, and I’d try to least expect it as quickly as the usual grieving process allows, so I could finally be completely and utterly taken by surprise with actual love, only offered to unsuspecting recipients. 

You see, when you are thinking about least expecting it, even if you are throwing yourself into hobbies and work and healing and are not on dating apps anymore… expectation is still with you. Because doing things to distract or better yourself is rooted in the original hurt. It’s hard to forget. Doesn’t matter if the expectations are wholly your own or society’s or a powerful suggestion from people who make their relationships public online. 

Expectation is a sticky shadow. I thought I could will it away, but the only way I ended up least expecting love was being absolutely hopeless. This state of genuine “given up” followed a couple years of trying to heal individually (impatiently, with expectations). I made progress, but I was still sad. I still am. Love doesn’t make your trauma go away. But it certainly makes the experience of living with it less lonely.

I’m not saying this is a universal truth. Point being, when someone tells you love happens when you least expect it, they may be omitting the fact that the easiest way to least expect it is to kind of be in the pits of despair. 

I always pictured when-you-least-expect-it as a time closely resembling the ‘girl who is going to be okay sequence.’ She finds herself in some new passion. Volunteering, running, or ceramics are classic. She throws out her ex’s t-shirt. She locks in at work. She initiates plans with friends or family again. And this is partially true. These things help. But it’s hard to let go of expectation of any kind when it’s connected to the self-improvement we’re told should immediately follow romantic disappointment. 

I’m not endorsing depression or stress or overwhelm as a way to detach yourself so much from when-you-least-expect-it, that you least expect it because your mind is consumed by sadness and leaves no room for anything else. But let’s introduce some nuance to rom-coms, books, magazines, strangers in club bathrooms and on TikTok telling us the moment lonely people find love is when they have given up because they found their own individual happiness. 

There is no great moment of enlightenment followed by the reward of romance. I had done enough work to be in decent enough shape to give it a try. But I didn’t think I had because I was still sad. 

I met the person I’m in love with during one of the worst weeks I have ever had mentally. It still doesn’t feel real. I followed the script first: I deleted the apps except one, pretty much stopped going out, and spent the past year throwing myself into (very queer) line dancing and adult ballet classes.

Nobody is more surprised than me that it worked. I ended up meeting the first person I’ve ever loved through the hobby I took up to try and literally move through trauma, get some endorphins, and decenter going out as my main source of community: at Angela Trimbur’s Dirty Dance Camp. 

Part of me hates that the cliché was right. Mostly, I’m relieved I just had to be patient. Still giddy that patience was rewarded with a love story that sounds made up. When I deleted Hinge, it was because the story of meeting someone on there felt mechanical, anti-climatic, and sad. I never wanted to permanently lose hope. 

My girlfriend and I actually crossed paths three times before I really took notice. But the day the best relationship of my life began, I almost didn’t get on the bus that took me there. I was so overwhelmed with work I hadn’t slept all week, I’d cried in public almost every day, and spent the entire bus ride on calls in the back, even though I was a bus captain (gay). 

My memories of the girl who noticed that I was not wearing a bra with my white tank top due to both queerness and the chaos of the week are fuzzy. I was buried in my laptop for most of the weekend. My friend Caileigh had to tell me to just get myself on the bus when I admitted I wasn’t sure if I could do anything other than collapse on my floor at the end of my week from hell. 

And that was how the universe caught a skeptical air sign by surprise with zero expectations. I had truly given up, I felt hopeless. And you need a little bit of hope to have an expectation you’ll eventually find love. 

I do not think hopelessness is the best way to relieve yourself from the pressure of a world that places partnership in equal (often higher) esteem with individual accomplishment. But I want to be honest about the fact that “giving up on love and dating” ultimately felt really fucking lonely. It took months of disappointment to reach a point of feeling so hurt I didn’t care anymore, I didn’t want partnership. I just wanted to feel better.