Valentine’s Day is here again and the air is filled with the sweet scent of love and bitterness. Much like a box of chocolates, Valentine’s Days come in many varieties. Some are as delicious as the heart-shaped coating promises us, and some, after we’ve taken an eager bite, are filled with that nasty-tasting stuff we hate and leave our fingers sticky with disappointment.

Whatever your status is this Valentine’s Day, I think we can all agree that the great thing about this holiday is, whether good or bad, it’s eventually over and then all the chocolate is marked half off. Here are a few of the best and worst Valentine’s Days I’ve experienced in my decade or so on the market.

  • Once when I was single, I took the subway all the way from Manhattan to Brooklyn to listen to an anti-Valentine’s Day poetry reading. After a 45-minute ride and a 15-minute walk in the snow, I arrived to locked doors and an advertisement that said the reading had been the night before. On the subway back to Manhattan, the girl seated in front of me had handful of balloons that kept hitting me in the face. She was too preoccupied making out with her boyfriend to notice, and the train was too crowded for me to move out of the way, so the balloons continued to hit me in the face for the next three stops until they got off (the train, you perv).
  • Once when I wasn’t single, my high school boyfriend hand-plucked roses he grew himself in his backyard and placed them all over my car so that I would find them in the morning when I walked out to leave for school.
  • Once when I was single, my dad had flowers delivered to my office building. The whole day everyone kept telling me my boyfriend had gotten me some really nice roses. I did not correct them.
  • Once when I wasn’t single, my boyfriend gave me a handmade card. At the time, for whatever reason, we likened our relationship to that of Calvin and Susie in the cartoon strip Calvin and Hobbes. He addressed it to Susie and signed it as Calvin. Seems a little cheese-ball to me now, but the me back then thought it was the sweetest thing.
  • Once when I was single-ish, I was going on a third date with a guy on Valentine’s Day. He didn’t acknowledge the fact that it was Valentine’s Day for the entire duration of the date, and neither did I.
  • Once when I wasn’t single, this guy who wasn’t my boyfriend showed up at my doorstep with an enormous bagful of Valentine’s Day goodies, including a huge stuffed love bug. He was a friend who knew I had a boyfriend, and it wasn’t one of those situations where I secretly wanted him to be my boyfriend. Awkward. I decided, in the heat of the moment, that the only thing to do was to help him save face by not letting him see that I hadn’t gotten anything for him (?), so I ran upstairs and grabbed one of those Valentine’s Day-themed mini M&M’s bags with the label on it marked “To” and “From” and wrote his name and mine. Looking back, that probably did not help matters.

You know how this works. I showed you mine, now you show me yours. Share your own happy/horror stories in the comments below while we await the always wonderful Half-Off Chocolate Day!

  • Alyssa

    LOVE these.

    My very first boyfriend forgot our first (and ultimately only) Valentine’s Day, which was devastating because we were long distance, and I had just started my first semester at college and was just sad, pathetic and lonely. So I ended up getting hammered on pink trash can punch at a friend’s house, like you do.
    However, he did feel terrible, so I got a card everyday for a week afterwards, which I thought was spectacularly sweet at the time. Mostly because I was 18 and even his breathing was spectacularly sweet.

    Then, about ten years later, I had just started dating a guy when we were at Elbow Room and he realized it was Valentine’s Day. I didn’t care, but he kept saying how bad he felt. Not bad enough to buy a $3 rose from the guys that kept coming in off the street to sell them, or to stop drinking top shelf scotch off my tab, but bad. Bad enough that he said he’d give me a piece of his art when I took him home. (He was an artist, he had no car.) Which he did, but what I didn’t know if that it was leftovers from a art show he had done in his last year of college, which was etching of convicted killers or something. So for Valentine’s Day, I got an etching of a dead murderer.
    Which was still fairly cool, because hey, art; but he didn’t even pretend to hide the fact that it was one of what looked to be a few dozen of the same person. Turns out, these were the ones not good enough to go in the show. So art, yay!; but Big Lots equivalent art.
    And he didn’t even sign it, so there go any Sotheby’s dreams…

    • Haha, thanks for sharing, Alyssa! Oh artists and leftover art and forgotten Valentine’s Days and disappointed expectations. I’ll drink to that — a huge solo cup of pink trashcan punch for old time’s sake 🙂

  • Elissa

    One year, when I was recently single on Valentine’s Day, I took the day off of work, bought a bottle (or a few bottles) of wine, about ten pounds of chocolate, and a few movies. I spent the day in my pajamas, inhaling chocolate and wine; alternating between love stories (Love Actually, The Notebook, etc) and horror movies (I Know What You Did Last Summer, Evil Dead, and any zombie movie I could get my hands on). All in all, not such a bad day!

    • What’s your poison? I usually go for a table bottle of red wine…but some things call for a handle of good whiskey.

    • Haha, sounds divine 🙂

  • Kelsey

    My birthday is 4 days before Valentine’s, so it’s been a mixed bag.

    First boyfriend: told me he wasn’t going to get me anything since we’d just celebrated my birthday. We were 16, and looking back on it, fair enough. But of course at the time I was distraught. What to do? I made him guilt-cookies, spent like 4 hours on these Valentine’s cut out sugar cookies and I remember saying these words to my sister “I hope he feels like shit when he gets these.” I put them in his locker and had a dozen roses by the end of the day.

    Second boyfriend: Cooked me a romantic dinner and lined his apartment with the pages of his journal from all the times he’d written about me. It’s only as I’m typing this that I realize how INCREDIBLY WEIRD that was. I walked around the combo living room/dining room/kitchen reading all the entries. (we were in hot and heavy l-o-v-e) We ate dinner and then decided to drive to San Antonio (from Austin) to walk down the river walk. We made it there, but it was very late, and on the sleepy, why-did-we-do-that drive home, he realized he forgot to PUT UP the journal entries before his roommate came home that night.

    Third boyfriend: Walked into my apartment with like three bags in his hands, pulled out this random box of chocolates and literally said “oh, here.” Sounds crappy but I don’t put a lot of stock in the holiday, and this was my favorite scenario of all. No muss, no fuss, still got the requisite chocolate.

    • Awesome stories, Kelsey 🙂 Love the guilt-cookies (high school luv…lol) and can totally see the look on that guy’s face when he realized his roommate would see all of those journal entries!

  • Kelsey Kruse

    I had a third date on Valentine’s Day one year. The guy took me to a restaurant, used a coupon on himself, and had me pay the rest of the bill because he “couldn’t really afford this place.” Class-act.