14 Awkward Proposals That Became the Best Part of the Story

A proposal often starts with a vision: a perfect setting, a meaningful speech, a flawless moment frozen in time. But real life rarely sticks to the script. These stories follow proposals that went gloriously off-plan, where love survived interruptions, mishaps, and a healthy dose of humor.

• My husband planned to propose on the beach on our holiday, and ordered the ring online 1 week before we flew. It didn’t get delivered til we were on the flight, 5k ring, delivered to a neighbour and we were away for 10 days in another country. My now stepson told me his dad was going to propose but to keep it a secret. So, for 9 days every sunset, every time he tied his shoes, I thought it was time... but no. He was acting shady the whole holiday and always checking his phone, it drove me crazy so on the last day I asked him if he had changed his mind. He told me the whole story, and on arrival back home he ran over the the neighbours in panic. They’d kept it safe, luckily, and he proposed in the forest the next day. © mrsfranky / Reddit

• My husband’s plan was for us to set up our Christmas tree and then he was going to propose to me in front of it. But after we finished up I wandered to the bedroom to go change into my lounging clothes and he called me back to the living room and I reentered without any pants on. He had to quickly hide the ring and tell me to go make myself decent. © Unknown Author / Reddit

• I was 18 and we were on a seaside holiday. We go out for a walk along the beach and I'm looking at some seagulls playing. I turn around and he is on one knee, I was in complete shock. Then I notice he is purposing with an empty box? I interrupted with 'Is there supposed to be a ring?' He looked shocked and panicked. It was so windy by the sea that the ring had been blown out of the box. I said yes anyways and then by some miracle we found it! He was pretty gutted that he had messed up the proposal for me but I didn't care. Since then we moved to a bigger city together to attend university, The wedding is in a few months time and I've just had our first baby. Couldn't have picked a better guy. © Unknown Author / Reddit

• We went on vacation to the beach about two years ago. I had suspected he was going to ask me to marry him, but when he didn’t do it by the end of the second day I figured it wasn’t happening. The reason being was because we had planned to go parasailing on the third day and honestly who brings a ring 200+ feet above the ocean?! Well, my husband does. The awkward part? I was seasick and threw up on myself after I said yes! Thankfully, they dunk you into the water right before you get back onto the boat so I was able to kind of clean myself up. Definitely a hilariously awkward story I can’t wait to tell our kids one day. © Chrisisab****forlife / Reddit

• My buddy’s girlfriend kept telling him that he couldn’t surprise her. After college, they were planning to move together to another town. About 6 months before graduation, he told her he wasn’t sure about the move or their relationship. She turned around to cry. He called her name, and when she turned back, he was on one knee. Did it to surprise her. © Unknown Author / Reddit

• My grandmother stopped a bad proposal; After a great night out, my grandfather said “the ring is in the glove box, if you want it”. She demanded he get out of the car and propose like a man. They were married for 60+ years. © TheShoeOnTheHighway / Reddit

• We dated for 5 years. He planned a rooftop dinner, candles, roses, my favorite song playing. He got down on one knee, hands shaking. I was already prepared to say yes. But there was a glitch in his brain, and instead of proposing, he blurted out, “I forgot the ring in the car. Don’t move!” He sprinted to the elevator, leaving me alone on the rooftop for 15 minutes. When he came back, sweating and out of breath, he dropped the ring twice. I laughed so hard I cried. He finally managed to say, “Will you marry me?” I said yes before he could mess up again. Our wedding speech included the security footage. Everyone died laughing.

• My parents where celebrating New Year and my dad in the emotion of the moment, said to my mom that he wanted to spend the rest of his life with her that why didn’t they get married. There was no ring... Just the thought and the moment. My mom said she was going to think about it. After a month of not mentioning the topic again and my dad all anxious about what did she have to think so much about, asked her if she had already had enough time to think. She asked “about what?”... Dad: “about we getting married” to which my mom answered “ohh that was serious?”. She then took another month to this time really think about it and said yes. 30+ years now and happily married. © karina_r_w / Reddit

• Friend of mine’s brother. He drove his girlfriend of several years to some part of the suburbs she was unfamiliar with and pulled up in front of a house she’d never seen before. She asked where they were and he said “It’s ours.” He’d gotten a mortgage and put down the down payment already. He proposed there in the car. She said no and dumped him on the spot. © Uberman77 / Reddit

• One day my bf’s mom and her mom decided to go buy a wedding dress. Later that day, she said to my bf’s dad “guess what I bought today” and showed him. Then he said “well I guess I better tell my mother we’re getting married”. Married for...over 35 years now. © isthisonegoodenough / Reddit

• I had a fancy date planned, we were going to a nice restaurant in the old town district and were going to walk around by the harbor. Everything was planned out perfectly, we were dressed up nicely and it was going to be an awesome night out. I had the ring in my pocket and everything. Then, as we are getting in the car, she suddenly says “You know what? I’m kind of tired, can we raincheck this? Maybe eat something quick and cheap in town?” So we went to Wendy’s. She polished off a baconator, and I handed her a ring. “I wanted to take you somewhere fancy and do this, but Wendy’s will have to do.” © ebonythunder / Reddit

• My mom was dating a guy from university, everything was serious, they loved each other, but his mother couldn’t stand her. This guy proposed to my mom. It was a beautiful evening, very romantic, he got down on one knee, took out a ring, and asked, “Will you be my wife?”
  Mom thought about it and said, “Yes.” But then he added, “Phew, great! Even though my mom wanted me to find a blonde...” And immediately she replied, “No.” And broke up with him.
  Now she jokes that she was one step away from a life with a weirdo. © Not Everyone Will Understand / VK

• I knew something was off because he kept asking if I was “having a good day.” Not sweetly, carefully. Like he was checking whether this was a bad time to say something serious. We were sitting on the couch, half-watching TV, when he muted it and said he needed to tell me something important. My stomach dropped. This didn’t feel romantic. It felt like a breakup. He took a breath and said, “You mean so much to me,” then reached into his pocket. I was bracing myself for whatever speech people give when they’re about to end things. Instead, as he pulled out a folded piece of paper, something else slipped out of his pocket and hit the floor. The ring. We both froze and stared at it. After a second, he groaned and said, “That was the speech. I was trying to pull out the speech.” Then he laughed, completely flustered, and said, “I practiced this and it sounded way better.” Then he looked at me and blurted out, “I love you. I want to marry you. I forgot everything else I was going to say.”

• Pilot here. A guy asked me to fly him and his significant other over a field, where 150 people had formed a heart and 2 rings. Huge show, I was really impressed.
  When she saw it, her response was, “Look at all those idiots! How ridiculous is that?” He did not ask his question that day. © apiratenamedbob / Reddit

Love doesn’t always go according to plan. Here are more proposal stories that had an unexpected twist.