Love & Sex

6 Stories About Awful Valentine’s Days

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Any film with the line "ass to ass" is not suitable for Valentine's Day.

Valentine's Day. For many people, it's a big deal. For others, not so much. As you gear up for tomorrow, take a look at these stories of rough Valentine's Days, and take heart. 

One Valentine's Day, my then-boyfriend cooked a wonderful dinner for us and then suggested we rent a movie. The movie we initially wanted to rent was out, so we decided on a film neither of us had seen but had heard good things about, Requiem for a Dream.

Word of advice: any film with the line "ass to ass" is not suitable for Valentine's Day. — Giana


I was having dinner with my girlfriend one Valentine's at the apartment I shared with Keith, my roommate from college, who was pursuing his dream of acting at the time. We were eating in the kitchen, so we heard Keith open the door and go to his room accompanied by… someone, but we didn't actually see either of them.

About twenty minutes later, his door slams shut, and high heels very aggressively clicked across the floor and out the door. A minute or so after that, Keith padded in, wrapped in a bed sheet and very obviously drunk off his ass. My girlfriend and I never did figure out what he did to send his date running like that, but we did find out, over the course of a very rambling forty-five-minute conversation, Keith's thoughts on love, life, and the nature of women.

We also found out the exact size and shape of his balls, which at one point fell out of his makeshift toga and came to rest on the chair. Somehow, Keith didn't notice, and continued. It was when his dick tumbled out, still clad in a holiday-appropriate red condom, that we finally burst out laughing. He rearranged himself with as much dignity as he could muster, and strode off to his bedroom, where at one point we could hear him reciting the "What a piece of work is man" speech from Hamlet. Dave


It was only the second time Connor and I were going out, which made it a little strange that it was officially a “Valentine’s Day Date.” But that year, V-day just happened to fall on a Saturday, so I pushed my usual skepticism aside and agreed to meet him.

I walked into the restaurant and up to our table as he was still removing his coat. We ordered some wine and opened with the usual small talk while skimming our menus. As the entrees arrived, we ordered another bottle.

By the end of the second bottle, the conversation had gone from a major project he was working on, to his ex-girlfriend of two years (whom he met online; she lived in Brazil, and they'd only met in person once during their entire relationship), to how he didn't support his younger sister's abortion. It was the most personal information I had ever received in such a short amount of time.

“How did we get on this, exactly?” I asked.

“Sorry, I know it’s kind of heavy for a second date,” Connor replied.

After paying the check when his credit card was declined, twice, I walked out of the restaurant thanking the universe for exposing this information sooner, rather than later. As I got in my car to drive home, I took a quick glance in the rear-view mirror. There was spinach (from our appetizer!) stuck smack dab in the middle of my front teeth. Figures. — Marisa


After months of chatting online, I decided to finally meet up this guy I had met on with the express purpose of losing my virginity. I was a freshman in college and he was thirty-two. We didn’t specifically plan for this to take place on Valentine's; I only realized what day it was after waiting outside my dorm for him to show up for a half-hour, watching all the hand-holding couples walking to the moderately-fancy Italian restaurants in walking distance of campus.

He wasn’t as attractive as his profile pic (nobody is), and within a few minutes in the car it was evident that the chemistry we’d established after countless chat sessions didn’t translate to real life. I was already regretting the evening but chalked it up to my usual social anxiety. I’d backed out of chances to have sex before, but after recently turning nineteen, I decided I could no longer afford to wait, so I ignored all of the evening’s warning signs. I ignored his comment about “not having fucked a teenager in years” pass, and I chose to ignore the fact that he lit up a half-smoked cigar minutes before kissing me. I didn’t even think twice when he mentioned that he’d previously worked in a London sex club/dungeon and still had some whips.

Eventually I found myself naked in his bed, bathed in the light of an empty fish tank. He told me that since it was my first time, I should drive the bus, which apparently meant I should suck him off while he didn’t move or make a sound. He came without warning, then drove me back to my dorm. The only silver lining is that since I’d given a blow job before, and we didn’t have anal sex, I didn’t have to consider that evening my first anything. — Alex


Valentine's Day fell two weeks after my boyfriend cheated on me, which signaled the end of our four-year relationship. My friend, who happened to be a former beauty queen and one-time contender for Miss Universe (I wish I was joking), dragged me to a mixer that night. It was unequivocally a disaster, as I watched her being hit on constantly while I stood awkwardly nearby, ignored and wobbly on my heels. I'd overcompensated for the night; I was wearing too much makeup and a dangerously low-cut top and push-up bra.

I finally bolted and returned to the apartment I had just moved into. I had no furniture and the boxes were still stacked to the ceiling. I spent the rest of the night lying on the floor, drinking vodka and listening to “Landslide” on endless repeat. — Milla


My friend was talking to a rather handsome, scruffy lawyer that seemed like someone I would kiss and never call again, while I was stuck with scruffy lawyer’s Drunk Friend.

Drunk Friend, clearly about ten shots of Jameson deep, slurred to me, “You know, I’m going home soon. I am. So. What is happening with this?” I responded that his advances were moot and I did not want to come to his apartment. I was polite.

Then he grabbed my ass.

I removed his hand and said “I am not going home with you. And please do not touch my ass.”

He replied “You’re a pain in the ass.”

I ordered a Maker's Mark, clinked glasses with him, rolled my eyes, and took a sip.

Drunk Friend looked at me quizzically for a moment and then said, “You’re a filthy Jew, you know that?”

I turned, grabbed my bag to leave and said to scruffy lawyer, "Your friend's an asshole. Have a great Valentine's." — Juliet


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