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10 Nightmare Proposals That Did Not Live Up to Expectations

Susannah Bradley is a freelance writer and editor based in Portland, Oregon. Her work has appeared in The Seattle Times, MSN.com and US Weekly. When not writing, Susannah can be found baking cookies. In her estimation, Snickerdoodles are...

When you have a dream proposal in mind, but it goes horribly wrong

The story of your engagement is one you'll tell over and over again for the rest of your life, but what if it's a tale you'd rather forget?

Maybe you were hoping for a sweetly sentimental declaration of love while he was envisioning viral stardom or maybe he half-assed it when you were hoping for a grand gesture. Or maybe, like a matrimonial Goldilocks, your proposal was just right. These 10 women weren't so lucky — read on for their cringe-worthy tales of indecent proposals.

What she wanted: To be surprised

What she got: Not the surprise she wanted

Corey D. and her boyfriend Mitch were living together in an old trailer in Grand Forks, North Dakota, when Mitch planned a surprise proposal. The trailer, which was at least 20 years old and had been given to Mitch by a family member, had a hallway so narrow that Corey and Mitch had to walk sideways through it.

Mitch’s plan was to hide in the bathroom, then pop out into the hallway with the ring. It worked a little too well. Corey was so surprised that when Mitch popped out, she shoved him backward with such force that he got stuck in the hallway. Corey had to throw her weight against Mitch’s body several times in order to free him. Bruised but unbowed, he then popped the question.

What she wanted: A weekend out of town at a fancy hotel with a romantic proposal over dinner

What she got: A ruined surprise

Julie F. from Nashville, Tennessee, knew her boyfriend Will was going to propose; it was just a matter of time. She had already told him not to buy a ring. Instead, Julie wanted him to ask her parents for the ring her great-great-grandmother wore.

Julie’s parents came for a visit shortly after the conversation about the ring — that’s when things went south.

“During the visit, I'm in the car with my parents and my dad turns to me and said: ‘Will asked me today if he could marry you. I told him that you're a grown woman and the decision is yours, not mine.’”

Though she’s happily married, she’s still sad that what should have been one of the most romantic events of their entire relationship was ruined by her dad.

More: Women Care More About Food Than Sex on Valentine's Day

What she wanted: A ring

What she got: A ring — for someone else

Valerie Shaw, who lives in Sydney, Australia, had a rocky, off-and-on relationship with her boyfriend Rick, but things had been really good for about six months. Valerie was sure that their problems were behind them. One day, while the couple was on their way to the beach, Rick pulled into a gas station to use the restroom. Valerie opened the glove compartment in search of a tissue and spotted a small velvet box. She couldn’t stop herself from opening it, and inside was a diamond ring, small but pretty, in an elegant white gold setting.

Valerie was so thrilled that she jumped out of the car, shouted “Yes!” and leapt into Rick’s arms as he walked back from the restroom.

Rick looked mortified and confessed that ring wasn’t for her. It was for his ex-girlfriend, whom he had recently started hooking up with — and who was pregnant. With twins.

When you have a dream proposal in mind, but it goes horribly wrong
Image: Getty Images

What she wanted: A proposal

What she got: A DIY job

“We both knew we wanted to get married,” said Lindsey B. of Alamo, California, “but he never got around to proposing. So, I put a note on the toilet that read, ‘When you're done pooping, will you marry me?’"

He said yes, and they recently celebrated their 16th anniversary.

What she wanted: A vintage ring

What she got: The wrong vintage

“My now-husband proposed with the ugliest yellow-gold ring from the '80s,” says Jessica M. from Ann Arbor, Michigan. The setting was an enormous asymmetrical blob, and the diamond was cloudy and yellow. The ring was considered a “family heirloom,” but it really should have been sold off or given away, not saved for someone’s wedding, according to Jessica.

Jessica’s husband was hurt that she didn’t want to wear the ring. Mainly, he was worried that his family would be offended if she refused to wear it. Jessica did wear the ring on her wedding day, but the ring she thinks of as her real engagement ring is a more modern one that she and her husband chose together. The '80s monstrosity still makes an appearance when Jessica visits her husband’s family, but otherwise, it stays in her jewelry box.

More: 6 Proven Personality Traits That Make It Easier to Find Love

What she wanted: A moonlit night and old-fashioned romance

What she got: Awkward jokes, drunken nudity

Jennifer J., an attorney in Portland, Oregon, had been dating her boyfriend Tucker for two years and had discussed marriage with him several times, when the couple went out to dinner with a group of his friends. During dinner, Tucker started making jokes about getting engaged, and about how maybe it wasn’t for him.

“He was just being a complete ass. I knew he thought it was funny but it honestly hurt. After dinner, I told him how disappointed I was that he had made me look stupid in front of his friends and how I didn't understand why he hadn’t proposed yet.” 

They went for a walk that evening and Jennifer recalls that the lighting was perfect; it was a beautiful night. It seemed like the awful jokes were just a setup and he was going to pop the question, but they walked and walked and it never happened.

Instead, Jennifer and Tucker wound up at a bar pounding margaritas. They arrived home late, and as Jennifer was taking off her makeup, Tucker suddenly appeared in the bathroom doorway, completely naked, with a ring in his hand. He got down on one knee and slurred a drunken proposal, which Jennifer accepted. Who says romance is dead?

When you have a dream proposal in mind, but it goes horribly wrong
Image: Endai Huedl/Getty Images

What she wanted: A private moment and a vintage ring

What she got: An afterthought

Alicia K. of Portland, Oregon, had lots of things to worry about, but getting engaged wasn’t one of them. She and her boyfriend Mike had been together for seven years and had three children together, but they couldn’t afford to keep a roof over their heads. So they were staying with Alicia’s sister. It was 3 a.m. and the entire extended family was still up wrapping presents and hanging out. Alicia was exhausted and needed to wrap the last few gifts before heading to bed, but Mike suddenly handed her a gift and told her to open it.

“I was sitting on the floor and he was leaning against the TV stand. As I open the gift to find a wedding set — both rings — I looked at him and he just said, 'Will you?' Within five minutes everyone was back to wrapping presents."

Though Alicia had never given much thought to marriage, she wishes her husband had planned a more thoughtful proposal and given her a ring in the vintage style she loves rather than the generic mall store set he chose. “Mostly, I wish I had a more romantic story,” said Alicia.

More: What Are the Five Love Languages?

What she wanted: A sunset proposal at the top of the Eiffel Tower and a dazzling ring

What she got: An I.O.U.

Hillary A. and Matt connected over their shared love of travel, and Matt had racked up an enviable number of frequent-flier miles. The couple had planned to use the miles for an international adventure, which Hillary was sure would involve a proposal.

Instead, one afternoon on a hiking trip, Matt presented Hillary with a pair of hand-drawn fake plane tickets and a cheap ring from Something Silver. He didn’t realize that his adventurous, outdoorsy lady actually cared about the ring, and he didn’t want to cash in his mileage points without first getting a “yes” from Hillary.

“I just wish he had tried a little harder to make it special,” said Hillary, who went out and bought her own ring — a 1.5-carat princess-cut solitaire in a platinum setting — just before the wedding. “Fake plane tickets and a silver ring don’t make for a great engagement story.”

When you have a dream proposal in mind, but it goes horribly wrong
Image: CSA Images/Snapstock

What she wanted: To feel like he couldn’t live without her

What she got: TFW you’re his only option

Sophie G. of Bellevue, Washington, was ready to get married, but her boyfriend Stefano was a confirmed bachelor. He often reminisced about being single, and he and Sophie had even had several awkward run-ins with women from his past.

Stefano had cheated on Sophie more than once, but she forgave him and hoped that she’d be able to bring him around. Ultimately, it wasn’t Sophie who convinced Stefano that marriage was a good idea; it was an STI.

“The herpes diagnosis was devastating for both of us. He saw it as the end of his attractiveness to women, and he was convinced that no one else would want him. I was incredibly angry that he never wanted to marry me until he found out that he had this disease. I was also incredibly relieved that he had not given it to me.”

In the same conversation where Stefano told Sophie that he had herpes, he asked her to marry him.

She said yes.

What she wanted: A question, a ring, a kiss

What she got: Ulterior motives

As Michelle was leaving her house one morning, her boyfriend put his arms around her waist and said, “I have a question for you. Will you marry me?” 

She said yes. “After giving me a quick hug, he went outside to smoke. He didn’t give me a ring or even a kiss.”

“I was running late for class, so he gave me a ride to school. I asked if we could meet up afterwards for a celebratory dinner.”

Turns out, he couldn’t meet her because he was being evicted from his apartment and needed to pack up his belongings. He assumed he could move in with Michelle since they were now engaged. The engagement, however, was supposed to be a secret, as her boyfriend kept reminding her not to tell anyone about it.

After the day of the engagement, Michelle didn’t hear from her boyfriend for days. And that was all the time she needed to change her mind about that engagement.

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