Olga G.
In the pursuit of love, numerous individuals have meticulously arranged heartfelt surprises, only to witness their romantic endeavors take unforeseen turns. Whether due to innocent mishaps or significant disappointments, certain gestures have either strengthened or strained relationships. Regardless of the result, some have chosen to disclose their romantic misadventures on the internet.

I emptied my wardrobe cabinet, and filled the cabinet portion of it and placed on the shelf flowers, chocolate, a stuffed bear, and numerous candy that she loved. When I told her to get my “hoodie” out of the cabinet, she opened it and said, “It’s not here”, and then proceeded to close the cabinet. © TheNote7 / Reddit
I was walking around at recess with my life-or-death crush, Christina, in 5th grade. I’d been planning this moment for weeks. She was a small girl. I told her she reminded me of strawberry shortcake. She asked why, and I responded, “Because you’re short and sweet.” She did not respond, and I’m still dead inside. © ikkyu666 / Reddit

Decided to make a bold move with a close lady friend. Invited her over for a home cooked meal on Valentine’s Day in my awful college apartment, since neither of us were seeing anyone (pretty smooth, right? I thought so). So I cook a pork loin and some pasta, and purchased an expensive $12 drink. “She’ll be here any minute,” I kept telling myself. At around 9PM, I texted her. She let me know that she assumed the invite was a joke. She did eventually sheepishly show up! We are now married, and I remind her of this every Valentine’s Day. © dumpsterKraken / Reddit
I got painting lessons for a girlfriend because she was getting into painting. She took it to mean that I thought her painting sucked. She never took the lessons and I never got my money back. © ccasella3 / Reddit
After the date I dropped her off in the parking lot where her car was parked, we said goodbye and no kiss, it was our first date. She got out and began walking across the parking lot and I suddenly got the courage to whip my car around, stop right in front of her, get out, and kiss her. In my head, it was like something out of a film. In person, I pulled up to her, forgot to put it in park, got out, walked away from the car, she looked at me horrified and pointed; I turned around and ran towards my car as it slammed into another parked car. Just a typical day in my life, really. © Unknown user / Reddit