Awkward Valentine’s Day Stories

Illustration: Gage Holbein

Love, lust and embarrassment. 


Valentine’s Day is most commonly spent with some sort of significant other and some form of a date, but how often do those dates actually go as planned? We know at least some of our readers have had a bad date and/or V-Day experience. In an attempt to empathize, we decided to compile a few of our favorite, and embarrassing, dates-gone-wrong stories of our staff members. Enjoy!


Last year my boyfriend and I got ice cream at Ivanna Cone for Valentine’s Day. I ordered vanilla, and he ordered Dutch Chocolate. He then proceeded to tell me that was his stripper name.


It was my freshman year.

I was convinced I was a city slicker and had an affinity for faux fur coats. One proudly hung in my closet, the product of an impulse buy, and waited for the perfect occasion to look especially bougie.

Well, that occasion just happened to be Valentine’s day. I had major heart eyes for this frat daddy heartthrob and knew he would be at the party I was going to later that night. Just like any other night I went out, I didn’t really want things to kick off until about 10 p.m. so I had a few hours to kill.

My grandpa doesn’t live far from campus so I called him to see if he wanted to grab dinner. He agreed and said he’d pick me up in fifteen for our grandpa/granddaughter date.*

Planning ahead, I figured it would be my best bet to wear my party outfit to dinner so when I got home I could lounge and drink bad alcohol with cheap chaser.

When my grandpa got to my dorm I asked him where we should go to dinner, assuming it would be somewhere nicer considering the occasion.

A quick 15 minute drive later we found a spot in the Pizza Ranch parking lot. Needless to say I was the only one in a fur coat there and got a ton of looks anytime I went back to the buffet.

The party also sucked and the boy turned out to be a dud too. The coat still looks great though and it started my love affair with fur coats that’s still going strong.

I guess it really wasn’t that bad after all.

*On a side note, my grandpa is a total riot. We go out to dinner a lot and every single time he tells me that he tells his friends he goes on dates with a younger woman (me) and lives with two others (his cats). He might, maybe want to stop saying this due to the creepy implication but I don’t think he ever will.


It was my first Valentine’s Day alone after breaking off an almost-two-year relationship.

I wasn’t desperate for a date but a close friend (he’s gay, and, yes, it’s pertinent to the story) was really keen on the idea of hooking me up with one of his “friends” (a guy he had a huge crush on but he wasn’t gay so it wasn’t going to work out). I was skeptical but I figured there was no harm in going out for coffee with another lonely soul.

He was cute, well-dressed and a theater major. I wasn’t really expecting much and I didn’t get much.

We met at the coffee shop and greeted one another. We proceeded to order our coffee. He ordered some sort of elaborate, dairy-filled, froufrou drink—a warning sign in itself. I ordered a black coffee.

First dates are always awkward—as soon as we sit down, it’s suddenly harder for me to breathe, my outfit now feels so constraining and I can’t sit comfortably. The space between us is tense and uncomfortable.

“So, [our mutual gay friend] tells me you’re a vegetarian; how’s that going?” he said.

“I guess pretty good,” I said.


“You know, that reminds me of this joke.”

He proceeded to tell me a JOKE that included graphic detail about a dead animal. How funny. How amusing. To tell to someone who’s sworn off meat for six years a joke about a dying animal. Hilarious.

“You know, I think it’s time for me to leave,” I said as I picked up my purse and coat. As if he didn’t get the hint he said, “Here, let me walk you back.” I insisted I was fine and that it was only a couple blocks away but, sure enough, he walked me back. Thankfully, he was kind enough to entertain me with depressing stories of dead family members.

I haven’t spoken to him since.


My boyfriend and I were roadtripping last year during Valentine’s Day, we decided to stop in Des Moines, Iowa (Iowa is always a bad idea) for a bite to eat that wasn’t greasy fast food and for an excuse to get out of the car for an hour.

Little did we know that almost every restaurant in downtown Des Moines closes at 5 p.m. on a Saturday night. Silly us. We used Yelp (also always a bad idea; this trip was a learning experience for both of us) to see what was actually open around us. Yelp found us this restaurant which it described as “casual dining,” which, to us, meant that our crusty selves dressed in jeans and sweatshirts were welcome there.

Of course, “casual dining” meant the exact opposite to Yelp. It also said it was relatively inexpensive–also wrong.

We naturally entered through the back door because front doors in Des Moines actually look like back doors. We sat down and the waitress handed us our menus. Menus without any prices next to food items.

The menu had no listed prices.

We both stared at each other. My boyfriend whispered, “This is bad.” The menu suggested that this was a three-course dining experience. He was right, this was very bad. We conversed and decided that our total bill was going to be $80 at least.

There was no going back: we had already entered through the back doors and our crusty selves were surrounded by middle-aged, upper class, well-dressed individuals and we had gotten waters. We were in a pickle.

So what did we do? We made a run for it and went back out the back door. We vowed never to stop in Des Moines again.


He asked me to marry him as Mr. Darcy tells Elizabeth Bennett he loves her. It was 11 o’clock on a Saturday night, and I wanted to go out. He, on the other hand, wanted to stay in, so we compromised on Cosmic Brownies, C-Store popcorn and Pride and Prejudice.

We spent the first few weeks of our freshman year straddling the line between friends and more-than-friends. I took this proposal as a declaration of our relationship status. He was my boyfriend because we made a deal on his roommate’s stained couch to get married when we were thirty if we didn’t find anyone. I lived in a bubble for three weeks. I was so excited to have a backup spouse that I overlooked our differences.

A few weeks into our agreement, my sort-of boyfriend told me he didn’t think we had anything in common and everything he told me–his major, his favorite movie, his opinion of his family–was a lie. After this traumatic event, it took me a few weeks to realize he wasn’t friend material much less future husband material.


I’ve been single on Valentine’s Day since 1995. Over the past few years, I’ve been fortunate enough to have a date with a tall, dark and handsome… bottle of wine. I’m not embarrassed about my relationship status, just the savage behavior that results from chugging merlot by the bottle. If you’re feeling “forever alone,” swiping left or deeply considering auditions for a reality dating show,  just remember, as Zayn Malik once said, “Because you can’t find a prince doesn’t mean you’re not a princess.”

(P.S. Zayn, if you’re reading this, I’m available!)


It was 7th grade, Valentines Day. I was hanging out with all my friends at a boy’s house (gasp) when he invited his friends over before we went to a basketball game at the high school together (so cool). This kid in my math class that I had been hard core flirting with, came over and started making some moves, which I appreciated but did not expect because he was a cute, little shy boy.

In front of everyone he decided to ask me out and I had to uncomfortably be forced into saying yes because the spirit of the day. On our way to the basketball game I was then forced to sit on my boyfriends skinny little lap and had to hang out with him the next couple of hours.
Needless to say, I broke up with him the next day because I did not have the heart to break his on Valentine’s Day. Have yet to have a date on V-Day since!

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