I Broke Up With My Girlfriend On Valentine's Day & I Don't Regret The Timing

I grew up fantasizing about perfectly romantic Valentine's Days: a candlelit dinner, Champagne, lavish gifts, and a good f*ck. I had many lame Valentine’s Days with my high school ex-girlfriend that didn’t live up to those expectations. We’d get one of our moms to drive us somewhere we could afford (which was NOT on brand with my dyke princess-ness) and insist that other friends were meeting us there.

When I met my next girlfriend, Grace, my freshman year of college, I was lit AF to celebrate Valentine’s Day as half a real adult. After we met, we hooked up instantly, fell in love, and moved in within two months of knowing each other (typical U-Haul lesbians — except all I had to do was carry my sh*t down the dorm hallway). Valentine’s Day was coming up quick, and we were both being extremely extra about planning it. She skipped class and took off work to cook all day, while I obsessively shopped. Our piles of presents were enormous.

We had the kind of Valentine’s Day I had always hoped to have. Grace pulled out all the stops: She set up a blanket fort with Christmas lights (very Tumblr chic), cooked homemade heart-shaped ravioli, and bought me a beautiful diamond necklace. Though we had only been dating for three months, we were sickly in love. Never mind the fact that we hardly knew each other’s middle names — we were completely enthralled with the excitement of a new relationship. I couldn't believe I had actually found another queer woman in suburban Long Island. That's harder than finding your jean size at Forever 21.

Stocksy/Katarina Radovic

It sounds over the top, but our celebration felt authentic. We weren't just acting out all the pre-conceived ideas we had about Valentine's Day — we really wanted to spoil each other. It was beautiful. But as time passed, our relationship grew more and more toxic. Grace would regularly upload #TBTs to our Valentine blanket fort, but we fought all the time. We might have been capable of buying each other lavish gifts, but we weren't acting like adults, and we couldn't navigate an adult relationship.

As our second Valentine's Day together loomed closer, I wanted to break up with her, but I didn't have the nerve. After all, I had finally gotten what I wanted — a hot girlfriend. I had been neglecting everything: writing, classes, my family. My older cousin, Nina, noticed my behavior. Nina always seemed untouchable and way cooler than me; she would distantly engage with me at family functions, but wouldn’t hang out with me as a friend. When she showed up uninvited to my house and asked me for drinks, I knew there was a problem.

"You don’t seem right," she said. "You’re dating a f*ckboy, aren’t you?"

Not only did I have to come out as a lesbian, I had to come out with the fact that I was in a terrible relationship that was sucking the life out of me.

I promised Nina that I would break up with Grace the next time I saw her, and in my heart, I knew I needed to. The next time I saw Grace happened to be on Valentine’s Day. She picked me up and passed me a small notebook. She had strung together pages, pasting in pictures of us and listing all her favorite things about our relationship. It should have been this beautiful, intimate moment, but it only made my desire to break up with her stronger. She hadn’t shown this thoughtfulness towards me since our first Valentine’s Day together a year ago.

As I tore through the pages, I felt bile rising in my stomach. As I read her favorite things about me and her favorite memories of us, the words of the pages blurred as my eyes threatened to spill with tears. I’ve felt fake before — for spray-tanning, getting lash extensions, and wearing two bras at once. But the hurt from pretending I was happy and that we were in a healthy relationship was too much of an illusion for me to keep up. Once I started crying, I couldn’t stop. Grace seemed annoyed. She kept signing deeply and tapping her fingers, waiting for me to finish.

"I want to break up, I’ve been wanting to break up," I cried. I kept repeating the same variation of that sentence. I was the sad kind of drunk, which is even worse than the angry drunk.

When we were buying each other frivolous gifts like chocolates and flowers and diamonds, at least we were authentically happy. But the deeper our relationship burrowed, the less real our love felt. It was like we were dating in reverse and nothing made sense.

Valentine's Day helped me face the ugliest truths about my relationship. The holiday is a milestone that helps you define your relationship. It's how you hook your f*ck buddy into committing to you. It's how you can tell if your boyfriend is just passing the time with you or thinks you're wifey material. And it's how I knew my relationship was based on lies and illusions.

Grace and I broke up that day, got back together later, and then broke up again. But even though that first breakup didn't last, I felt empowered by summoning the nerve to break up with her on a day that's supposed to be full of love. I'm glad I finally worked up the courage to end a broken relationship, regardless of what the date on the calendar told me to do.

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