Skip to content
Search AI Powered

Latest Stories

The Absolute Worst Ways To Propose To Your Partner

Strange wedding proposal
Photo by Gift Habeshaw on Unsplash

Reddit user aloe_veracity asked: 'What is the worst possible way to propose?'

From our friends and families' own cringy stories, to the tales captured on social media, we've all witnessed our fair share of proposals that totally missed the mark or were just plain awkward.

In fact, most of us have come across so many of these stories, we all have an idea of what the worst proposal in the world would be.


Redditor aloe_veracity asked:

"What is the worst possible way to propose?"

Stealing the Spotlight

"At someone else's wedding or wedding reception."

- N-y-s-s-a

"I had to stop my friend from doing that. One of the nicest dudes ever, just a little naive."

"Fortunately, this was before the wedding, I didn’t slap the ring out of his hand or anything like that. I just very clearly told him it was a bad idea whilst at the pub."

- Polite_as_h**l

Clearly a Subplot from 'Grey's Anatomy'

"Arrange a fancy date night with your girlfriend, including dinner at a posh restaurant."

"In the middle of the meal, fake a brain aneurysm. Bite into a concealed blood pack, collapse, and fall onto the floor, the whole bit. A 'doctor' or a 'nurse' planted at an adjacent table rolls you onto your back, checks you, and says that you're not breathing and you have no pulse."

"He or she rips open your shirt to apply a defibrillator... revealing, 'WILL YOU MARRY ME?' written on your chest in red body paint."

"Pull out the ring, and say, 'I can't live without you, baby.'"

- Thatimensfaa

So Romantic

"Chucking the ring at them and saying, 'Here, wear this.'"

- Kai6180

"My friend got engaged like this and thought it was so cute for some reason. They did not last."

- Bada**Bumblebee

Wedding Dress Included

"My mom told me that my cousin’s girlfriend got tired of waiting for him to propose (apparently he said he would but hadn’t gotten around to actually doing it) that she straight up bought a wedding dress and told him they were getting married."

"He said, 'Okay.'"

"I believe they’ve been married for about 20 years now."

- PorkrindsMcSnacky

So Nervous

"My husband proposed to me while I was driving. At night. On a very busy, twisting road."

"He had a big proposal planned but then got super nervous and kind of just blurted out the proposal while we were in the car."

"We celebrate our 25th anniversary this fall. My thought was if I had the power to make him THAT nervous, I was in a pretty solid position."

"Honestly, it's not how you're asked; it's who's doing the asking."

- Neener216

Worth Waking Up For

"Mine might be the worst. I was a broke 19-year-old and thought that if I can't spend money on a good proposal, I'd go with the element of surprise."

"I woke her up at 3:00 AM and gave a speech about how we were going to be together forever and propose."

"Her response: ARE YOU F**KING KIDDING ME...'"

"We've been married 14 years this October."

- the_navillus

Red Flags in the Morning

"I got woken up an hour before my alarm clock rang. He just came home from visiting his parents for the weekend."

"No elaborate speech, just a 'Now or later?'"

"Me, being an unarticulated zombie for the first hour after being woken up, managed to mumble, 'Now.'"

"I got the ring stuck on my finger. It was slightly too small. And then I just went to work."

"Later that day, he reminded me that I still 'have to' say yes. Of course I did."

"A day later, colleagues figured out he never asked. He just demanded. So I told him to ask me, but he said since I already said yes, he didn't need to."

"After a little back and forth, he asked."

"I should have seen that red flag waving in front of my face, but it took two years to see it."

- Mondfairy

Practical Purposes Only

"This is the story of how my parents got engaged."

"Dad: Hey, you should move in with me."

"Mom: No. Not until we're married."

"Dad: Okay. Fine. Let's get married."

"Mom: Wait. Are you seriously asking me like this?"

"Dad: Yes. Why not. Marry me and then you can move in with me."

"And then they got married."

"It did not go well."

- biddily

Short and Sweet

"Proposing via text."

- Salty-Entertainer-29

"will u marry me?"

"k."

- aloe_veracity

Public Proposals

"For me personally, the worst would be any grand gesture around people. I’d rather you ask during a cozy night on the couch."

"My ex and I just talked and knew we were going to do it. We picked up the ring together and were walking out of the store. He bent down on his knee at a bench, and no one was paying attention. I’ll never forget how precious that was to me."

"I was at a large music festival last year and saw a guy propose to his girl quietly in the back of a crowd. No one seemed to notice that either, but I saw it and started crying to myself at how beautiful it was. She was snuggling into him the whole rest of the set."

- ApprehensiveBanana07

Quite the Rebound

"Say the wrong name. Other than that, you'll be fine."

- shipsaway9

"Something similar happened to a family friend. Someone she met online proposed to her within weeks of meeting her with a gorgeous diamond ring."

"She got caught in the moment and said, 'Yes.' It was at a fairly busy restaurant and everyone started clapping and cheering for them."

"When she got home, she took off the ring to send us a photo of it, and that's when she noticed that there was someone's else initial engraved on the inside."

"Turns out that the guy's ex-fiancee had broken up with him just months before their wedding. He met my friend online and decided to ask her to marry him instead out of spite and possibly because he didn't want to lose his deposit on the wedding venue and catering."

- Dane_k23

Fooled Ya

"Propose after being caught cheating."

- BeneficialSomewhere

The Argument to Win Them All

"While in an argument about wanting the get married, bring out the ring and just say, 'Here.'"

"A friend of a friend was 'proposed' to this way and thought it was the cutest. The red flags were waving themselves."

- royal_rose_

A Different Take

"Propose from prison."

- No-Art-9083

"Propose in prison."

- aloe_veracity

"Propose ON TOP of a prison."

- Ok_Wave_7359

A Jarring Experience

"Shock them by proposing to them right after they've told you that they've lost their job."

- BroadcasterX

Proposing or being proposed to is supposed to be one of the most special moments in a couple's life, signifying all that is to come. Imagining how someone could approach this moment in some of these ways is really staggering.

More from Trending/best-of-reddit

James Talarico
Jason Fochtman/Houston Chronicle via Getty Images

GOP Strategist Tries To Smear James Talarico With One Of His Old Facebook Posts—And It Backfires Spectacularly

Texas state Representative James Talarico is the Democratic nominee for Texas Senator John Cornyn's seat in the 2026 midterm elections. His Republican opponent will be decided between the incumbent Cornyn and controversial, scandal-ridden Texas Attorney General Ken Paxton after a run-off slated for May 26.

Talarico has been part of his home state's legislature since 2018. Before that, he was a middle-school English teacher and an executive director for a Texas nonprofit focused on bringing technology to low-income classrooms.

Keep ReadingShow less
Callista Gingrich
Vatican Pool - Corbis/Getty Images

Trump Ambassador Dragged After Seemingly Facetuning Herself In Official Government Video

Callista Gingrich, the U.S. Ambassador to Switzerland and Liechtenstein and wife to former Republican House Speaker Newt Gingrich, was criticized after she appeared to Facetune herself in an official government video marking the SelectUSA Investment Summit.

The 2026 SelectUSA Investment Summit will be held in National Harbor, Maryland, from May 3–6, and offers opportunities for companies, investors, economic development organizations, and industry experts to network and invest in the United States.

Keep ReadingShow less
Screenshot of Donald Trump
@Acyn/X

Trump Rips Himself With Self-Own For The Ages In Push For Presidential Cognitive Exams

President Donald Trump told on himself after he explained why he thinks prospective presidential candidates should be required to take cognitive exams—seemingly oblivious to all the concerns about his own cognitive decline.

Trump was discussing his administration's pledge that Social Security benefits would be tax-free in an appearance before senior citizens at The Villages, a prominent Florida retirement community, when he made the claim.

Keep ReadingShow less
Donald Trump with King Charles III in the Oval Office
Samir Hussein/WireImage

Someone Asked What Trump's Oval Office 'Interior Style' Is Called—And The Responses Are Hilariously Brutal

Following President Donald Trump's meeting with King Charles III in the garishly-decorated Oval Office, X user Volodymyr Tretyak, who offers regular commentary on the Ukraine war, asked others to name the "interior style" of the space to hilarious effect.

Charles addressed a joint meeting of Congress on Tuesday, becoming only the second British monarch to do so after his mother, Queen Elizabeth II, who spoke in 1991. His speech came as Trump has repeatedly criticized British Prime Minister Keir Starmer over Britain’s refusal to back the U.S.-Israeli war on Iran.

Keep ReadingShow less
Hilary Duff
TheStewartofNY/FilmMagic/Getty Images

Hilary Duff Shares Simple Yet Powerful Mantra Amid Worrying Weight Loss Trends—And Fans Are Applauding

Content Warning: Body-Shaming, Weight-Shaming, Body Image Issues, Eating Disorders, Skinny Trends

Millennials who saw Cheaper by the Dozen, The Perfect Man, and A Cinderella Story have always known that Hilary Duff was that girl.

Keep ReadingShow less