10 People Who Tried to Be Romantic—and Failed Miserably

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..

 

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  • 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
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  • 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
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  • 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

 

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  • 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.

10 Vacation Mishaps That Could Be Turned Into Hollywood Dramas

Vacations don’t always go as planned, and sometimes, they take a turn so dramatic they feel straight out of a Hollywood movie. From unexpected travel mistakes to shocking discoveries, these unforgettable mishaps are cringe-worthy, cinematic, and absolutely educational if you are planning to travel anytime soon.

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  • “Arrived in Mozambique with only South African Rand. I thought I’d be able to withdraw some cash from an ATM or pay for the visa on arrival with card, but for some reason my card wasn’t working. I couldn’t get into the country because I didn’t have the correct currency to pay for the visa, and my cards weren’t working to withdraw any cash. Luckily a kind person behind me offered to pay for my visa and I was able to get into contact with a family member to help check on my cards and activate them. It was one of the most touching moments of kindness I’d experienced, and also a lesson to always always always carry enough cash on you while traveling.” — Explorer_Waste / Reddit
  • “When I solo traveled in India and was ready to fly out of the country, I didn’t include my middle name when booking the flight ticket. Since the name on my ticket didn’t fully match the name on my passport without the middle name, I wasn’t allowed to board the flight until I called the airline company and had them change it. It was like 4 AM and the company phone lines weren’t open until a later time, but luckily I had like 4-5 hours before my flight departed and was able to have it changed in time.” — JollyManufacturer / Reddit
  • “I mistakenly assumed ‘Departure time’ was ‘Boarding Time’. Luckily, there was bad weather at the airport so the flight was delayed and I was able to board.” — ergosumdre / Reddit
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  • “Booked a tour in Nicaragua that was supposed to cost $52 USD. The guy who was working the credit card machine had no idea how to enter the converted rate amount. Ended up with a $5200 charge on my card. Luckily my CC company easily reversed the charge.” — da_london_09 / Reddit
  • “I booked a room in Paris for the 22nd but booked my train there for the 21st so I needed emergency accommodation for my first night there. I put in a hotel reservation online, chose the cheapest non-refundable option and then, once it was paid for, realized I had booked it for the next month by accident. $100 dollars I couldn’t get refunded, I ended up staying in a smelly, crowded 12 bed hostel room with a bunch of teenagers which cost $70, but it was all I could find.” — Unknown Author / Reddit
  • “My first time flying out of the country I was 16 and traveling alone. It was my first time on a plane. I got up to use the restroom and the woman beside me told me to take my passport (not sure why she couldn’t have watched it for me). I somehow promptly dropped my passport into the toilet where it slipped through the toilet crack and into the… well…A flight attendant tried to retrieve it (god bless her) but with no luck.” — Kokomo_27 / Reddit
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  • ’’I had planned a trip to Mexico to meet a friend. When it was time to fly home, I got to the airport and tried to use the check-in kiosk. It didn’t work for some reason. I went over to the help desk, gave them my info, and after some confusion, they dropped the horrible truth on me that I had booked the correct day of the week and time, but a week prior. I’d probably messed up by selecting the correct date while booking, then the page getting reloaded or something and I was in a rush to get through my previous steps, though I’m not sure how I missed the date in the emails the airline sent me.’’ – SuperSquashMann / Reddit
  • “Left my passport in the hotel safe when flying out of Prague. Didn’t realize this until I was at the airport, 90 minutes away from my hotel and no way to do the round trip in time to keep my flight. Contacted the hotel, made arrangements for another cab to bring me my passport. Got my passport and tried to check in for the flight, but they wouldn’t let me because it was now less than an hour to departure and an international flight. I could have just checked in on my phone while waiting, but didn’t realize it would be an issue. Ended up spending another night in Prague.” — ford_chicago / Reddit
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  • I was on a solo trip to Japan after a bad breakup. I got lost and my phone ran out of battery. When I finally arrived, the hostel was closed at night and locked with a 4-digit code, which I had saved on my dead phone. But then, by some miracle, despite having only seen the code once, I was able to remember it and let myself in. — therico / Reddit
  • I got pickpocketed hours before my flight to London from India. I had to pay the fee for overstaying my visa and missed my flight. Whatever little money I had, I spent it on trying to contact my dad. While waiting for his response, stranded in a foreign country with no money, I was forced to sleep on a bench, and it was cold. People passing by kept staring at me. Then a scary-looking man approached me and offered me a place to stay. Thinking things couldn’t get any worse, I agreed. But when we arrived at his home, I was shocked to see his wife waiting for us. She had prepared me a warm meal and told me everything would be okay. I felt like crying. The old couple asked me to sleep in the spare room they had. It was cozy and homely. Next day, the man helped me get to Western Union, where my dad had sent the money. Finally, I was able to rebook my flight and leave, but not before thanking the kind people who saved me with a few gifts. Forever grateful to them.

Vacations are more fun with family. However, a woman had to exclude her daughter-in-law from her family trip due to tensions between them

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