Fifth time’s the charm: Woman makes boyfriend ‘redo’ proposal

A 24-year-old man came to Reddit concerned that his future bride was already a bridezilla, before they’d even planned the wedding.

The poster wrote in the Relationship Advice forum on the site that he wasn’t sure what to do after proposing to his girlfriend four times. The problem wasn’t that she said no, but that she kept asking him to redo the proposal so she’d have a good story.

“At the [first proposal], my girlfriend said that she would love to marry me, but she had been looking forward to a more elaborate proposal. I assured her that I’d sort something out,” the boyfriend started out.

At the time, he understood, because he’d proposed without a ring while they were in bed. So a month later, he finally got the ring and set up some candles in their apartment to surprise her when she got home.

“Well, my GF loved the ring (thankfully) and teared up with happiness. She said that she really appreciated my effort, but what she meant by ‘elaborate’ was something original that she could tell our kids about one day,” the poster said.

That’s two strikes, so the boyfriend planned a romantic three-day vacation to their favorite city. He went all out with a photographer, 5-star hotel and a quartet.

“When I asked her to marry me, my GF said ‘yes’ and I thought all was well. Except when we were alone again she gently told me that she didn’t think now was the ‘right time’ and she was so worried about her future/COVID-19 that a proposal now wouldn’t be a good memory for her,” he continued.

At this point, the boyfriend decided to just ask the girlfriend what she’d like the proposal to look like. Each time he’s proposed, she said “yes” and then returned the ring, waiting for the perfect proposal.

“I’ll know when the right proposal comes,” the girlfriend told him.

Frustrated, this very patient man decided to try a fourth time with a home cooked meal. It was simple and sweet and he thought maybe going the less extravagant path was what she was looking for — in between asking her in bed without a ring and proposing in front of a professional photographer.

“She asked me if I was ‘trying to propose’ and I asked her what was wrong with that. Once more, she told me that she can’t wait to marry me but it still wasn’t quite the proposal she needed,” he said.

Turning to Reddit, the boyfriend asked whether he should try for a fifth time or whether he should figure out a way to deal with her insisting on a “perfect” proposal.

A lot of responses seemed as equally frustrated as the poster was.

“Tell her you’ve proposed 4 times already, and you’re done,” the top comment reads. “Either she’ll accept the ring or she won’t, but you are through jumping through hoops.”

“I would just be done with that woman,” someone responded in agreement.

Others pointed out that this could be indicative of a larger problem between the couple and the relationship overall.

“‘I’ll know when the right proposal comes.’ Translation, it will be right when it comes from a different guy,” one person boldly replied.

“It seems like she keeps hoping a proposal is gonna make her want to marry him,” another Redditor said.

The poster filled in everyone with an update a day later, saying that after reading the responses, he sat his girlfriend down to talk it over.

“My girlfriend looked somewhat nervous at that so I pushed her to communicate properly,” he said. “From her perspective, while she had responded positively to the idea of marriage prior to this, it had still been too soon for real engagement.”

Luckily, there seems to be a happy ending (and another proposal).

“We’ve now agreed that it’s better we’re both on the same page when it comes to proposing. We’ve decided that we’re both going to sit down and work together to make the proposal special for both of us,” he concluded.

Enjoy reading about relationship advice? Check out In The Know’s advice column, Group Chat, here.

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