13 Times “Will You Marry Me?” Turned Into “We Need to Talk”

A marriage proposal is meant to be a joyous milestone, but these unforgettable tales prove some love stories have a very different ending. What follows the big question isn’t always tears of joy; it can be painful rejections, shocking secrets, or sudden betrayals. You won’t believe the reasons these cringeworthy proposal fails led to a painful reality check.

• “Mom went to visit Dad and his next door neighbor asked, ’I don’t mean to pry, but what are you and (Dad’s name)? Like, are you dating, engaged, what?’ And Mom said that was a good question, and asked Dad, ’Your neighbor wants to know if we’re dating or engaged or what.’ He asked if she’d like to be, she said ’engaged, you mean,’ he said that was what he meant, and she said yes, and they went to buy a ring.” ©eclectic-worlds / Reddit

• “I was in Costa Rica on a hike to a big waterfall through an animal conservation place. A guy also hiking asked if I could take a picture of him surprising his girlfriend with a proposal. He was so nervous.
  We kept walking by small water features and then eventually a larger man-made waterfall. He gave me the signal and walked her under this glorified fountain and proposed. It was sweet and all, and she said yes.
  A few more miles into the hike, we saw the real giant waterfall. It was awesome. The look on his face when he saw it was pure disappointment, like he had really screwed up.
  I pulled him aside and reminded him that she said yes and didn’t know his plan. He told her how sorry he was for screwing up. I hope it is now a funny story in their happy life.” ©oscarbutnotthegrouch / Reddit

• My friend Adam proposed to his girlfriend after 4 years together. He couldn’t understand why she was angry about the way he proposed, so he showed me the video.
  I was at a loss for words when the video started with his girlfriend on a gym machine. She looked shocked, said yes, but after a couple of minutes, her smile seemed forced.
  Later, she told him she didn’t like the proposal, which upset him. He asked how I’d feel if a guy proposed at the gym. I said I’d hate it and understood her reaction. He called me shallow and a bad friend.

• “I know of someone who proposed to his girlfriend while she was sitting on the couch, tired from working a 12-hour shift, shoving a Big Mac into her mouth. He just walked up, opened the ring box and held it at arm’s length to her, saying nothing. Apparently he told everyone he proposed to her in the park while on a picnic.” ©davidgrayPhotography / Reddit

• “Friend of a friend proposed to his fiancée immediately after her grandmother’s funeral. The logic was sweet, but deeply misguided: her family lived across the country, so it was one of the very few times her family would be all in one place. Additionally, he was planning to ask her at a romantic dinner the week before, but those plans fell through when her grandmother took a bad turn.” ©Unknown author / Reddit

• “7 years ago my sister’s boyfriend bought a ring (too small) and just kinda gave it to her while they were on a bridge. He didn’t even make eye contact, and then turned to her, gestured at the ring and went ’and?’ She said yes, but they haven’t gotten married yet.” ©YasminEatsApples / Reddit

• “Walmart parking lot. After they loaded up their groceries, he asked if she wanted to take a little walk. She was bewildered and worried about the milk, so she agreed to a lap of their parking row.
  About halfway down the row, he nelt down without saying anything and showed her the ring (on the plus side, it was a really cool ring). At one point, I think she asked for a redo proposal, and he knelt down randomly and said, ’Will you marry me’ while they were packing Christmas decorations.” ©doodle_rooster / Reddit

• “The worst one I ever witnessed was a dude who brought his girl to Fenway park, and proposed on the Jumbotron. She said no, and the entire park erupted in laughter. I didn’t feel bad for the guy.” ©Inourmadbuthearmeout / Reddit

• “My SIL told me about a couple who she knew that got engaged while on vacation. It was some sort of tropical destination where he would have had any number of good proposal opportunities.
  They were in the living room area of their suite watching TV after a long day, and he started picking at his toe. Apparently, he had something weird going on with a toenail and asked her to get him the clippers from the bathroom because he didn’t want to walk on it.
  She got up to get the clippers from the bathroom, and he followed her and got down on one knee in the bathroom and proposed. She said yes. No backstory, no follow-up, that was just how he decided to propose.” ©Affectionate_Pea_811 / Reddit

• “I proposed on the summit of a mountain that we climbed together. It was insurance against her saying no... She needed me in order to get back down.” ©k*****jr / Reddit

• "I proposed to my wife in Times Square on New Year’s Eve (I was going for maximum cheezy!). She was pretty emotional and took a while to believe I was serious (even though I had a ring). This being New York, strangers started shouting at her to “HURRY UP LADY, WHAT’S IT GONNA BE? WE DON’T HAVE ALL NIGHT.” ©Unknown author / Reddit

• I once proposed to a married woman years ago. I don’t think it was terrible, just a little different.
  We were out at dinner, waiting for our food, when I asked to see her promise ring. I started messing with it and pretended it got stuck on my pinky. She began to panic, thinking we might have to cut it off.
  That’s when I said, “Or... we could just replace it.” I pulled out a new ring and asked, “With this... will you?” She said yes.

• My father proposed to my mother after his grandmother’s funeral. It was a weird move, honestly. My mom always romanticized it, saying he was trying to bring new life from death. I never really bought that story.
  Turns out, he was in deep trouble. My grandmother had a will that none of us knew about. She left behind strict conditions; if my dad wasn’t married by the end of that year, he wouldn’t inherit the family home.

We’ve all heard a cringeworthy story or two. Have you ever witnessed a proposal that went completely wrong? Share your own stories of unexpected moments and relationship drama in the comments below! And for your next read, be sure to check out our article on 9 Manicure Ideas to Try This Autumn Before They Get Too Trendy.