In sixth grade I had a crush on a girl and I wanted to send her a rose (something the school did), but I didn't want her to know it was me (my handwriting is incredibly distinguishable and I was really shy), so I paid one of my friends a dollar to write her name and "Happy Valentines Day, From Your Secret Admirer" on the card.
He went to the desk set up at lunch and turned in the card. Everyone at my lunch table watched as one of the teachers delivered the card to the girl.
We continued to watch as she smiled and giggled with her friends. She then jumped up and ran to the desk where they were selling the card/roses wrote some stuff down and then ran back to her table.
A few moments later, the teacher got up and walked over to my table, and she gave a card to my friend that I paid to write the note. It was from the girl—she had recognized his handwriting and wanted to go on a date. He got up and went to her table and accepted the offer.
—lostfan815
In high school, I was crazy about this one girl. But she had a boyfriend, so I stayed firmly in the "trusted friend" category.
Well, early February comes around, and she breaks up with her boyfriend! We plan to meet up for dinner a day or two before Valentine's Day. I'm stoked. I buy her a Valentine's Day teddy bear, and I'm seriously gonna ask her out, tell her my feelings, etc.
Well, I pull up to her house, and she comes out, and the first thing she says to me is, "Me and my boyfriend got back together, aren't you happy?!" That. Sucked.
—account deleted
My boyfriend of a year broke up with me over the phone while I was visiting my dad in another city. An hour later, my mother called sobbing because she'd had a knock-down-drag-out fight with HER boyfriend. My stepmom had been verbally abused and then called into work by her heinous boss (it was a Saturday).
My poor shellshocked father, dealing with three crying women, tried to make it better by taking my stepmom and me to a movie at the end of the day. My stepmom was really late getting out of work, so we missed the movie we wanted to see and settled for something none of us really cared about, just so we'd have something to do.
After the movie, we went to dinner. My dad dropped my stepmom and me off in front of the restaurant and then pulled around the corner to park and was hit by an oncoming car. He was fine, but the car was totaled. Worst Valentine's Day ever.
—hangoneveryword
It wasn't a bad date for me, but I was there to witness her worst date. We went to a botanical garden and we were having a good time when suddenly one of her heels breaks off. No problem. I take it and straighten the nail and bang it back so it's at least walkable.
Not even 10 minutes later, the clasp on her handbag breaks and all of the contents spill out of her bag. I'm handy, but I wasn't able to fix the clasp, so she basically had to football carry it the rest of the time.
So we're laughing about the tough luck she has and something small hits her on the top of her head. There was an elevated Japanese garden next to the path we were walking, so we thought a little kid was throwing tiny pebbles. We ran up to catch the kid, but as we were running, I see the top of her head and realize it was not a pebble but bird crap on her head.
I didn't want to alarm her, so I didn't tell her about it and told her to stop and come over. I grabbed a leaf and wiped the crap off her head the best I could. She realized what it was and she was MORTIFIED.
I couldn't help but basically laugh in her face. I wasn't laughing at her, but it was so hilarious that I couldn't contain myself. I reassured her that everything was alright and sometimes sh*t happens.
I went on another date with her the next week, but she was so shy and embarrassed that we didn't meet again.
—devidual
I was set up on a blind date when I was in high school with my friend's boyfriend's roommate. My friend failed to mention that the guy she was dating was pushing 30 and his roommate was the same age.
I was very uncomfortable about it. After dinner, my friend wanted to go back to her apartment to chill. I tried to ask to be taken home, but she insisted it would be a good time.
When we got to their apartment, my friend and her bf went to their room to do god knows what, leaving me alone with this creepy older dude. I felt extremely uncomfortable and tried texting my friend to take me home, but she ignored me.
Finally, after about an hour, I started petting their cat. I'm very allergic to cats. I then proceeded to rub my eyes until they swelled. This is when I burst into their room to show them my swollen face and insisted I be taken home. And she did right after that.
—swordfishing
Not exactly a date, but in Freshman year of high school a girl I had a huge crush on agreed to go to Winter Ball with me (basically semi-formal dance in winter).
We walk inside, she immediately ditches me and even tells me she only went with me for the free ticket (like $35 each) and proceeds to start making out with a random senior she'd never met from a neighboring school who came as someone else's date.
The joke is on her though, as all of her friends realized what a jerk she was, and I got slow dances with all six of them because they felt so bad for me.
I hung out with them throughout the night and never regret what happened. Worst experience at first, but the night ended very well.
—razakka
It's our first date and I take her to a movie. Then, we went out to eat at an Italian restaurant. During the meal, I feel my stomach start bubbling.
Later, her friend calls her and says she locked her keys inside and needs her to come let her in. Her apartment was a good 30-minute drive. When we leave, my stomach is making some noises, and I'm feeling it.
Halfway through the drive, it hits me—I'm about to crap my pants. So, I'm speeding to her house, with the windows down and the radio cranked so she can't smell or hear my involuntary farts.
Finally, we pull up to her apartment, and I ask if I can use her restroom, to which she replies, "Of course!" We walk up to her apartment door, and it's open with a large group of her friends waiting for her.
It turns out that it was a surprise birthday party for her. Without wasting any time, I make haste for the bathroom. The bathroom is rather small, with an accordion door, and it's located right across from her bedroom.
But I cannot help it. I sit down on the toilet and unleash the wrath of God on this thing. I could not have been quiet no matter how hard I tried. I'm in there for a good 10 minutes—I finish, flush, and wash my hands.
I walk out to her and three of her friends standing there, with the most disgusted looks on their faces. So I just said," I gotta go!" I left and that turned out to be our first and last date.
—reflectorbelt
Was with the guy for 2 to 3 years at that point. First, I know he straight up forgot about Valentine's Day as he shows up with a $5 gas station gift of a single fake flower and a pack of peanut butter cups.
Now, before you call me shallow, the gas station was directly next to my apartment building and I saw it earlier the same day. Pretty positive he swung by there on his way over. The make-up gift was an earring and necklace set. Yay right? Wrong. My ears are NOT and never have been PIERCED.
—etcetera
I routinely get awful gifts (never received a good one). Highlights have been:
- A whole heap of nothing (the usual, even with girlfriends)
- A mix cd I later found on her playlist listed with the title "James' Birthday Mix" (with James being her most recent ex)
- Ladies argyle socks
- A cheap pint glass with a pink bear with outstretched arms saying, "I wuv you THIIIIIIS much!"
- A Winnie the Pooh coloring book
- A 3-dollar stuffed frog from CVS with sewn-in lipstick prints on his cheap, fugly face and holding a cloth rose.
These gifts wouldn't bother me so much, except in each of these cases I was dating the girl for a significant period of time. The girls all took V-Day very seriously (otherwise, silly gifts are welcome) and I wound up spending a fortune on them.
—jonny_lube
Blank store-bought Valentine's cards. He said he didn't know what to write. Like a kid making an excuse for not doing his homework.
—knowingcat
Someone telling me they got a present, then waiting for Valentine's Day to go, "Oh, well I told you I got it for you because you were sick and I wanted to cheer you up." Does that count?
—jes1001
I wasn't seeing anyone at the time but I received a big box of chocolate strawberries. They're actually my favorite! But it came with no note. So I spent ALL day trying to think who would send me strawberries.
My ex from a few months ago? The guy I went on a few dates but fizzled out? A secret admirer? And I didn't exactly want to call any of these people up and ask. Ah, the suspense! Turns out my aunt had sent a box to all of her nieces. Best "worst" gift ever!
—tomorrowme
A stuffed dog and a sweet, heartfelt declaration of undying love...that was written for the guy that she just broke up with to be with me. She just figured, "F*ck it, it's already written and sealed." She even scratched his name off the envelope and wrote mine. We didn't last long.
—bowyer-betty
