Valentine’s Day Bloopers: When the pressure’s on and we fall short

February 13, 2019

By Jessica Eyre

Valentine’s Day is just around the corner. And it’s a big deal. According to CNN, for Valentine’s Day 2018, approximately 144 million cards were exchanged, an average of $143.56 is spent per person, $4.77 billion total spent on jewelry alone.

Not to mention the candlelit dinners, flowers, chocolates, and unmentionables that can all be part of the gig. And if you’ve ever been to the movies, you know that a grand gesture is almost expected.

That’s a lot of pressure!

And sometimes the pressure is too much. And to prove it, I gathered stories from people that show how Valentine’s Day can go wrong, just so no one feels like they’re failing alone. Names have been changed to protect the guilty.


A “refreshing” Valentine’s Day gift
From “Vanessa”

I was 22 years old and finally, FINALLY, I had a steady boyfriend for Valentine’s Day. Now my longtime dreams of roses, chocolates, adorable stuffed animals and romantic dinners were going to come true. What I got, however, was a nightmare-inducing gift that morphed into an office practical joke.

After spending the afternoon in Las Vegas, my boyfriend–let’s call him Franz–and I started the two-hour drive home. Franz reached for something in the backseat and produced a plastic bag. “Hey,” he said, “Happy Valentine’s Day!” He then handed me the bag.

It was heavy and awkwardly shaped. What I found inside was a glass Mason jar filled with red and white Starlight Mints. But that wasn’t what was so unusual about it. Atop the jar’s typical canning lid was something I had never seen before, and haven’t seen since.

The top of this jar was a plastic doll’s head, with the type of face that a sweet little grandmother might crochet around to craft homemade baby dolls. This doll face, however, stared back at me with its painted, blue eye-shadowed eyes and lipstick, with a collection of more Starlight Mints designed to create a halo of hair. Jauntily atop this refreshing “hair” sat a straw western-style hat.

“I was reporting on a craft fair at the senior citizen center today and I saw this and thought I’d buy it for you.” Franz said. “Can I have a mint?” And he then plucked a mint from the doll’s ‘do.

I honestly didn’t know what to think of this gift. Was he trying to hint that I had bad breath? Did he legitimately think this was a great idea for a fun Valentine’s gift? I knew my friends would be eager to hear my stories of a romantic night with Franz. How would I explain this? Mortified, I ended up sneaking the gift into the condo I shared with friends and hiding it under a pile of blankets in a closet.

And that is where the doll stayed for many months. Until one day when my roommate found the doll and was honestly frightened. At this point, I was no longer dating Franz, which meant this doll quickly became a source of many laughter-filled nights. In fact, wanting to get rid of the doll, I “regifted” it to a fellow co-worker. Equally horrified by the doll, he found inspiration for a great, decades-long practical joke he played on another co-worker. Even when the victim moved from Utah to Florida, that Peppermint Head found its way to continue the torment.


Somewhere, anywhere, nowhere
From “Claire” 

Our first Valentine’s Day as a couple, we both had jobs where we worked in the evening. But we made plans to go out. And that’s about as far as it got because I thought he was making reservations somewhere BECAUSE IT’S VALENTINE’S DAY, but he thought we could just drop in anywhere.

After going to just about every restaurant in the area, we got into a fight (the biggest fight we’ve ever had), gave up, and he dropped me off at work. I got in my car, went to a drive-thru by myself and ate before going back to work. I don’t remember a lot of details, just that I was so mad.

This was the first and last time we attempted to celebrate this holiday.

We have used that fateful Valentine’s Day as a reminder of the importance of communicating better with each other.

A borrowed gift
From “Diana”

Our first year of marriage, my husband wrapped up library books. He had them displayed like was some kind of romantic god. He thought he was being so sweet and kind, thoughtful and frugal. I didn’t think it was any of those things.

The second year, he had my sister pick out a sweater for me. While it was a great sweater, his presentation kind of ruined it. He came into our bedroom, handed me a GAP bag, and I pulled out a man’s sweater.

“Oh, that one’s mine, sorry. Yours is in there, too.”

He’s never lived that one down, either. I was his first girlfriend. He’s needed years and years of training.


Dinner with a crowd
From “Dustin”

We thought we could have a romantic dinner with our 5- and 1-year-old kids. I won’t go into details, but no amount of ambiance can combat a dirty diaper or food used as projectiles.


What secret admirer?
From “Lindsay”

I got an idea from one of those ridiculous romance books to role-play as a secret admirer. I planned a dinner at the park and wrote a note to my husband asking him to meet me for a scandalous affair—in my handwriting—and signed it some other secret name. I left it on the steering wheel of his car.

I watched him read it, look around awkwardly, and then throw it away. And drive home. He never mentioned it. I had to bring it up. Oh, and my park picnic was ruined.


From “Cheryl”

I got pregnant on Valentine’s Day. Does that count as a blooper?


Be specific
From “Heather”

I had big expectations for the first Valentine’s Day with my husband. But I just expected him to know that about me. I told him all I wanted to do was spend the day together. Here was his idea of what that meant:

We stopped by his parents’ house on our way to lunch (dinner would be too crowded), and his younger brother wanted to come. Sure! The more the merrier. While we were there, his mom gave me some of my husband’s things that she was cleaning out, including a scrapbook he made for a previous serious girlfriend.

After lunch, with brother in tow, we went home and did chores. Chores. I went to bed and cried because I wanted to get dressed up and get flowers or be the recipient of some romantic gesture, but he thought he did great because we did indeed spend the entire day together. Meanwhile, I was now in possession of the scrapbooked evidence that he knew how to be romantic.

We have used that fateful Valentine’s Day as a reminder of the importance of communicating better with each other.

The common thread through all of these stories is that even though someone fell flat on their face in the romance department, they found humor and forgiveness. Eventually. Happy Valentine’s Day to all the lovebirds out there, and may you be more successful than this crowd.


Jessica Eyre is a writer and marketing strategist. She loves movies, going to see live music, and has a firm belief that most any life situation can be related to an episode of “Seinfeld.” She is a mother who does her best “I’m interested” face when hearing about the latest YouTube video her kids want to re-enact for her, and yet, at the same time, finds them to be the most interesting people she knows.


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