A (Brief) History of Valentine's Day
- Catherine Moscatt
- Feb 14, 2024
- 4 min read

Happy Valentine’s Day. I am both proud and ashamed to admit I have had some wild Valentine’s Days. Or maybe they just seemed wild to me. I always liked Valentine’s Day because why treat it as a boring old day when you can get and give cards, flowers, chocolate and balloons. It’s like a mini Christmas and it’s not just for the sweethearts, okay? Anyone can celebrate Valentine’s Day.
First Valentine’s Day
Age: 16
This was my first parent approved relationship. The guy was named….let’s call him A. I was home from school sick when Mom came into my room with a big package I had received in the mail. It was my first Valentine’s Day card from a boy, a large box of chocolates, and a stuffed turtle with adorable big glass eyes. It was the perfect Valentine’s kit. I had a chocolate a day for a month and made it last until we broke up. The stuffed turtle went into the back of the drawer so I wouldn’t have to see him and cry.
Most Shameful Valentine’s Day
Age: 17
A bunch of us were celebrating Valentine’s Day by playing Spin the Bottle at the library. I was sitting between two boys, going back and forth, kissing both of them. At one point, one of the boys took me into a secluded hall so I could give him a lappdance. The other boy was stuck with me after everyone else left, waiting to get a ride. I stood up and he slipped his hand beneath me so when I sat he fingered me through my leggings. I jumped right back up. First of all the abruptness was painful. Maybe he didn’t mind random things shoved in his orifices but I kind of did. He was sending me weird vibes saying if I didn’t comply he could hurt me. My mom arrived just then and I jumped in the car. I should have told her, or at least the library director. The next night was a Valentine’s Day dance at my youth group. I should have gone but I didn’t. I just cried and pretended to be sick. That was a hard year.
Most Disastrous Valentine’s Day
Age: 18
I was seriously dating another guy. Let’s call him B. We had a beautiful Valentine’s Day together. I felt like a princess in a lovely blue and sheer dress. We ate at a diner and exchanged presents. That evening we went to our friend’s house for a Valentine’s Day party. I overdid it a little. Okay I overdid it a lot. I puked all over my boyfriend, the floor and into a mixing bowl. I don’t know how my friends put up with me back then. I was so intoxicated I blacked out in the shower. Everyone was desperately trying to get me sober before curfew. I went home wearing my friend’s clothes and told my parents I spilled soda on mine. I miss that dress. My friend’s mom threw it out. She never liked me. I hope she cleans her mixing bowls well.
Saddest Valentine’s Day
Age: 19
Now I was away at college, still dating B but the relationship was fizzling. He got jealous, I got flirty (especially when I was drunk) although I never went so far as to cheat on him. But we were growing apart. The plan was for him to come up Valentine’s Day weekend but I think that meant different things to both of us. To me it meant go out, get plastered and watch Deadpool in theater. He had a panic attack and hid in the bathroom. Note: Most of my boyfriends are introverts and I am probably the biggest extrovert you’ll ever meet. We broke up three days later. It was for the best but an occasion like that will never stop being sad.
Harsh Valentine’s Day
Age: 20
This Valentine’s Day I was in the mental institution for the second time. I was forced to take a medical leave of absence from school, I wasn’t speaking to my best friend and the day just passed like any other. There is no such thing as ‘happy Valentine’s Day’ in a mental institution. Although I did speak to my crush on the phone.
Painful Valentine's Day
Age 21 and 22
I was involved in a long distance relationship with C. I don’t want to talk about C.
Lonely Valentine’s Day
Age 23 and 24
Several family members were ill with cancer (one terminally so) and a pandemic was raging. My parents left a balloon and a Winnie the Pooh card at my spot.
In Between Valentine’s Day
Age 25
A few days before Valentine’s Day, I went on an amazing first date with a charismatic, sweet, adorable, sexy guy. But then Valentine’s Day happened and I was like “Do I text him? Would that look desperate?” Dating in the early stages is so confusing.
Best Valentine’s Day
Age: 26
My boyfriend (let’s call him my boyfriend because he’s still my boyfriend) took me to an amazing restaurant. The service was delightful, the food was great, and he brought me flowers. I had no alcohol and felt amazing.
Casual Valentine’s Day
Age: 27
Due to car situations, my boyfriend and I are not celebrating on Valentine’s Day. We will celebrate the special day alongside an even more special day: our two year anniversary. But we are going to a Gothic Masquerade Ball so I’ll let you know how that goes. And cross my heart and hope to die, there will be no mixing bowls.








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