Valentine’s Day is a polarizing phenomenon. For some, it is a pinnacle of romance, with proposals peaking on Valentine’s night. Couples get cozy, and the atmosphere becomes “romance-saturated.” The “red on red” aesthetic creates a utopian scenery of gift cards, flowers, and heartwarming SMS messages.
Recently, I went through my thick, burgundy high school diary. It reminded me of the days when boys threw splintered paper flowers and handwritten letters into the air. Some were sweet, but others? Others were just plain weird.
If you think your dating life is awkward, take a seat. Here is a breakdown of the weirdest Valentine requests I’ve ever received, analyzed for your entertainment.
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1. The Musical Botanist
“Roses are red, violets are blue. On this Valentine, be my rose flower and I’ll be your violin.”
We have all heard the “Roses are Red” trope, but this takes a sharp turn into a linguistic cul-de-sac. Usually, the second half of that poem rhymes with “blue.” Instead, this young suitor decided to pivot to string instruments.
I remember staring at the paper, waiting for the “chills” to hit. They never came. Instead, I was hit with a wave of confusion. What does it mean to “be someone’s violin”? Does he want to tuck me under his chin and rub a bow across my ribs? Is he suggesting I am high-maintenance and need tuning? Is there a secret romantic connection between roses and violins I’m yet to discover? It has been years, and I am still searching for the romantic symbolism. This remains the gold standard for “weird.”
2. The Heart Arrhythmia
“Will You Be My Val? My heart skips a beat when I see you, but I want it skipping more.”
This came from a school senior. The choice of words takes me straight to “Cartoon Land,” where the weirdest lines are supposed to make sense. While “my heart skipped a beat” is a classic romantic cliché, the desire for it to skip more moves the conversation from romance to the Emergency Room. Sir, if your heart skips any more, you don’t need a date, you need a doctor.
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3. The “Pity Me” Proposal
“I just need someone to hangout with for Valentine. I’m depressed seeing my friends make plans. Let me spoil you for a night.”
Reading between the lines, I pictured a young man desperate to impress his circle by showing up with an “emergency girlfriend” in a red dress. Do people actually get depressed about Valentine’s Day? Absolutely. But using your own FOMO (Fear Of Missing Out) as a pickup line is like trying to put out a fire with gasoline. It’s the highest level of “pity invite.”
4. The Brutally Honest Reminder
“Happy Valentine! I don’t have a girlfriend and you don’t have a boyfriend. Can we go to the Genesis Theatre and see a movie?”
The invite was cool, but did he really have to add the second line? There is a fine line between “refreshing honesty” and “accidental insult.” This request walked right over that line and kept going. It felt like a direct “Ouch, thanks for reminding me”. Total lack of finesse.
5. The “Pressing Issues” Meeting
“Your space teeth perfects your smile. Bless my day with your ever-smiling face… I want to sit face to face with you and discuss pressing issues.”
This started so well! “Space teeth” (a gap-toothed smile) is a specific, endearing compliment. It felt personal and observant. But then, the wheels fell off.
“Discussing pressing issues” is what you do with a landlord, a lawyer, or a Prime Minister. It is not what you do on a Valentine’s date. What were these issues? Climate change? The school’s curriculum? The geopolitical stability of West Africa? My romantic “off button” was hit so hard it nearly broke.
6. The Refund Policy
“I already booked a seat for two but my girlfriend suddenly broke up with me. Can you go with me to the event?”
This one created a swirl of mixed feelings. Part of me felt terrible for him, who gets dumped a week before Valentine’s? But the other part of me was baffled by the logic. He wasn’t asking me on a date because he liked me; he was asking me because the ticket was non-refundable. Asking me to be the “replacement part” for a pre-booked seat is a high-level weird request.
