Valentine’s Day is fast approaching, and this will be yet another Valentine’s Day I find myself single. For years, I’ve had a complicated relationship with this day, ironically making it the longest relationship I’ve ever been in.

Valentine’s Day is fast approaching, and this will be yet another Valentine’s Day I find myself single. For years, I’ve had a complicated relationship with this day, ironically making it the longest relationship I’ve ever been in. During early adulthood—my formative dating years—Valentine’s Day was something I dreaded, because I wanted badly to celebrate it with someone I loved and who loved me. The weeks leading up to it felt like torture, because I knew it wasn’t going to happen. Of course I was always aware of how foolish it was to care about a non-denominational made-up “holiday”. I constantly reminded myself of the corporate greed, the complete meaninglessness of it. However, knowing this didn’t stop the billboards, commercials, and other people everywhere from constantly reminding me that it was happening. No matter where I turned, a giant red heart that in no way resembles an actual human heart, loomed near and made me feel even more alone. For years, this day was a symbol of my unhappiness, when my worst fear seemed to be realized: I was unlovable. That’s why, if an opportunity bearing even a passing resemblance to romantic love came my way on this day, I would latch onto it regardless of how destructive or idiotic I knew it would be. In my mind, doing anything with someone who might be attracted to me was better than being alone at home, wallowing in self-pity.

The first instance of this was Valentine’s Day my senior year of college. I remember my roommate was off doing something cliched and romantic with her boyfriend. I was home alone, lying on the pull-out bed of my couch and watching television. Around midnight, I got a text from someone who hadn’t been on my radar for a while. I’ll refrain from using his real name so let’s call him Samson, because why not?

Samson and I had been close two years prior to that midnight text, during my sophomore year of college. He and I met at a party, clicked instantly, and saw one another almost every day. I became infatuated with him, assuming he might be equally interested in me. He drove me to his hometown and introduced me to his mother, invited me to concerts and parties with him, and even bought me dinners. I let this go on for months before finally confronting him about why the hell we acted like we were dating, but had never even kissed.

“We’re just friends,” I remember him saying. Of course, I was crushed.

At this point in my life, I was too terrified to make the first move. Every day I waited for him to tell me that he was interested in me, but it never happened. I tried convincing myself that he was shy, or waiting for me to say something. Today, I would never think to let something like this go on, let alone for several months. However, at this age, I was not only scared, but I had little confidence in myself. I remember finally confronting Samson after a night of way too much alcohol. We were in my bedroom. He was spending the night, and didn’t want to sleep on my bed with me.  I asked him something like, “Are we dating? Do you want to date? Do you like me?” He acted completely shocked, as if this coming completely out of left field. “We’re just friends,” I remember him saying.

Of course, I was crushed. Reality came crashing down on the sham. We distanced ourselves from each other after that, and he began dating a friend of mine, a girl he met at one of my parties. Within a month of knowing one another, they were in a relationship and stayed together for nearly two years.

Now back to Valentine’s Day, two years later. Samson and his girlfriend had been broken up for a few weeks, and he texted me very late at night that he wanted to see me. If this had been any other night, I probably would have ignored him. I didn’t want to see him, but my desperation to not be alone on Valentine’s Day trumped that. I got in my car, and drove over. We drank and caught up, then he suggested that we watch a movie. Of all the movies he had in his collection, he went and chose the Larry Clark movie Kids. If you haven’t seen it, Kids is a tremendously sad film about a bunch of teenagers who contract HIV. In other words, the perfect film to watch on Valentine’s Day. After the movie, we were both drunk and I asked him if I could sleep over. He made room for me on his bed, and we began kissing. This led, almost inevitably, to some highly regrettable and anxiety-inducing sex. I woke up the next morning feeling awful, not only hungover, but also deeply unsatisfied. I left without waking him. I didn’t see the point in engaging with him any further. I knew that our night together meant nothing to him and that I meant nothing to him. Even still, my lack of self-esteem had me count this as a small victory. My first Valentine’s Day doing something.

On another Valentine’s Day around two years later, I had a new opportunity to spend it with someone, anyone and ignored all red flags in order to seize that opening. I was living in Oakland at the time, and had been briefly hanging out with a man who I’ll call Captain (again, why not?) Captain was interesting, and sort of cute. We had a few things in common, but I wasn’t all that attracted to him. I was ready to end things until he asked me out for drinks on Valentine’s Day. I weighed this against spending the night alone and found it to be the better option, and we met at a bar near my apartment. After two rounds and some small talk, Captain asked me something I had never been asked before on what was technically a first date: “Can I move in with you?” Yes, you read that correct. Captain wanted to live with me, after only knowing one another for two weeks! It felt like the universe was playing some sick prank on me. You’ve wanted to be in a serious relationship all your life, so here it is. I told Captain the truth: I didn’t think we were romantically compatible. He then told me his truth: he had nowhere to live because his roommates kicked him out of his apartment due to his heroin addiction. Definitely did not see that coming. I told Captain he could crash on my couch until he found somewhere to go (and I also urged him to get help), but he never took me up on that offer. To this day I don’t know whatever came of Captain, but I hope he got the recovery he needed.

After that, I gave up on Valentine’s Day. Instead of yearning to make that night special, I went the opposite route. I denounced it, waving my metaphorical middle finger directly in its face. For the next few years I put on a good show. I pretended that in no way at all did I care about this day, and that I loved every ounce of being single. I turned it into a festival that celebrated my total disgust with love, disguising my bitterness as independence. Essentially, I was lying to myself, but in a completely different way. Shockingly, this wasn’t helping my self-esteem all that much either.

It was around this time maybe two years ago I was in one of those mall jewelry stores for tweens (don’t ask why) when I started fiddling with some nostalgic mood necklaces. I came across one whose charm was a perfectly kitsch Yin and Yang symbol. As I stared at the changing colors, it dawned on me: why was only capable of identifying with one extreme or another? As long as I was filled with violent longing for the perfect day, or violent rejection of the whole institution, I was never going to have a good day.

What I’ve come to learn now, after all this time, is that Valentine’s Day is not good or bad. Rather, it’s good and bad. It took a lot of mistakes, but I’ve finally learned that I’m allowed to yearn for love while also embracing singledom. I’m allowed to feel both disappointed and content when I’m alone on this day, or any other day for that matter. It’s not exactly the philosophy behind Yin and Yang, I know. I’m sure ancient Chinese philosophers did not have a single twenty-something who had watched one too many romantic comedies in mind when they created it, but it works for me.