10 People Who Tried to Be Romantic—and Failed Miserably

We’ve all seen grand romantic gestures in movies—roses, candlelit dinners, and heartfelt love notes. But in real life? Things don’t always go as planned. From cringe-worthy proposals to lovely gestures that backfired, some well-meaning romantics have ended up in laugh-out-loud disaster mode.

If you’ve ever attempted to sweep someone off their feet and tripped instead, you’re not alone. Here are some of the most awkward, embarrassing, and downright disastrous attempts at romance that prove love isn’t always smooth sailing.

• Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself.
  The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began. - Krell47 / Reddit
• Set up a date with a girl I had class with the previous term, she mistook me for a different guy she liked with the same first name in her cell contacts list, then she spent half the date waiting outside for this "other guy" while texting me saying, "Where are you? I really don't want to be stuck here with this guy I used to have class with!" - Jollies / Reddit
• I was trying to chat up a cute girl at a checkout counter. The conversation had organically faded out, and we were both just kind of standing there awkwardly, her waiting for me to leave. But I was oblivious and didn't want to stop talking, so in a desperate attempt to keep it going, I blurted out, "I bought a comb today." She looked at me like I was a complete idiot (not wrong) and I shamefully walked out of the store. - H0use0fpwncakes / Reddit

• Met a guy at a bar, and we hit it off. He asked me out on a date and told me to dress up very nicely as we would be attending an art gallery opening. I got all dolled up and when he came to pick me up, he was in a t-shirt and jeans.
  Some of his friends were there, but he wouldn't introduce me to them and proceeded to chat with them and ignore me the entire evening. After we left, he asked if he could take me out to dinner. I figured, whatever, at least I'd get a free meal out of this. We hit up a nice pizza joint and ordered a pizza.
  As I reached for a second slice, he just looked at me and said, "WOW! A second slice? Really? Jeez, you're a house!" So I ate the rest of the pizza. - etothepowerof3 / Reddit
• A couple months ago, an old friend of mine was coming into town. We spent a lot of time together in high school, I had a huge crush on her, but we were always dating someone else. Anyway, we end up going to her friend's place, we have a decent time.
  On the way home, I figured I'd fess up and hope for the best. I told her that I was really nervous about tonight because I always had a huge crush on her. "Oh, wow. Uh, I never knew. Well, yeah...". She wasn't interested, and in turn lost a longtime friend. - doctorsound / Reddit

• A girl I had previously been with and I still talked nearly every day since we broke up years ago, but now she was at college two hours away. So, I was going to put it all on the table for Valentine's Day.
  She had a busy schedule, so I decided to go in early morning, I took two kittens and two dozen roses and went out there and sat in the back seat with her, amongst the kittens on a bed of roses and proceeded to talk to her from what I (foolishly) tried to memorize. We were close enough that it wasn't completely awkward, but still just wasn't happening. - anarkingx / Reddit
• Was at a festival, and went over to talk to a girl I was interested in. For some reason I tried to get her attention with a water bottle, that was unknowingly open. I soaked her with it. There is no coming back from that. - AzusmattyboyTM / Reddit
• I spent six years secretly, yet not so secretly, in love with one of my good friends. One night he kissed me...and it continued for about a week or so. And over that week I guess I just couldn't contain my happiness about it and I just told him how I really felt. I then got the "I never meant to lead you on" speech. And now I basically trust no one. - Lady_Rugger / Reddit

• A really hot boy has been flirting with me at work, and I'm terrible at it. When he finally asked for my number, he gave me his phone to type it. My mind went completely blank, and I just stared at it for 30 seconds.
  Then instead of putting in my number, I panicked and started running away. Yes, with his phone still with me. He ran after me, shouting my name.
  He eventually caught up to me and said, "If you are not interested, just say that. Don't have to run from me like that." He took his phone and didn't talk to me again.
• I was on a vacation with my girlfriend. Woke up needing to use the toilet urgently. My stomach was making horrible noises. My GF always starts her day with a shower, so to not stink up the bathroom, I snuck out to use the lobby toilet.
  When I came back, she was in tears. Crying about me leaving, saying what if someone broke in, why I didn't tell her I was going, what if something happened while I was gone, to me or her, etc. I tried explaining myself to her, but she didn't care, and insisted I should have woken her up, left a note, just gone in our bathroom, etc. - Direct_Wishbone4931 / Reddit

Here are 10 vacation mishaps that can be turned into Hollywood movies.