Woman Keeps Demanding Boyfriend Propose Until He Does It Right: “After 4 Proposals, I’m Lost”

Proposing to the person you intend to marry can be a daunting task. Nowadays, 57% of Americans discuss engagement for about a year before a proposal happens, but that doesn’t make the anxiety go away. What if your partner says “no”? What if they swallow the ring you put in their glass of champagne?

This guy can at least say that he tried – four times at least! Each time, his girlfriend accepted but said she wanted a fancier, more elaborate proposal. After he pulled out the big guns and booked a five-star hotel, dinner, and an opera quartet and she still wasn’t satisfied, he began thinking that something else might be wrong.

A man was at his wit’s end with his girlfriend after four unsuccessful marriage proposals

Image credits: Timur Weber/Pexels (not the actual photo)

Each one was not up to par with her standards, as she didn’t feel it was the “right one”

Image credits: Vitaly Gariev/Pexels (not the actual photo)

Image credits: Timur Weber/Pexels (not the actual photo)

Image credits: Houssam benamara/Pexels (not the actual photo)

Spontaneous proposals are out, as many couples start planning their wedding even before a proposal happens

Once upon a time, proposals were spontaneous. A couple would be sitting on a park bench silently, a partner would get on one knee with a ring, and the couple would be engaged. Nowadays, more people seem to want spectacle over spontaneity.

It’s not just about wedding planning; lots of couples plan their engagement nowadays, too. According to the 2025 Zola Wedding Trends Report, many couples start booking venues and making other wedding arrangements before a proposal. The moment of the engagement is almost a rehearsed event as well, as 70% of couples discuss the timing and the circumstances together.

The good news (or the progressive news) is that the proposal doesn’t fall entirely on the groom anymore. Modern couples look at the proposal as a more collaborative moment. 53% of couples say they shop for an engagement ring together, and if the proposal goes south, they’re not afraid to redo the moment. In fact, 8% of couples said they had a counterproposal, and another 8% wish they had.

The time of the proposal matters a lot. People want to celebrate the good news with those closest to them; that’s why most couples prefer the holiday season as the best time to propose. Christmas is the most favored time of year to get engaged, with Christmas Eve, December 23, and even New Year’s Eve trailing a little bit behind.

There’s nothing wrong with the bride proposing to the groom. Granted, it’s still a very rare occurrence, as only 2% of women proposed to men in 2022, according to Zola. Although 98% of women view themselves as equals in the relationship, 77% of those in heterosexual relationships never considered that they could be the one to propose.

Image credits: Jessica Teal/Pexels (not the actual photo)

A perfect proposal should be about the relationship and the love story between the two partners

Proposals and weddings are like desserts: each person has their favorite and the one they hate the most. There’s no magic formula that will make a proposal a perfect one. In fact, a perfect proposal doesn’t really exist – it all depends on the two people who are getting married.

Some people might prefer a calm, intimate environment, while others might think it’s the coolest thing on Earth to be proposed to at a sports game. As professional proposal expert and proposal planner Michele Velazquez told Bored Panda in a previous interview, it all depends on what the person and their partner want.

“The key to a successful proposal is to create a proposal concept that would be meaningful and resonate with your partner,” Michele said. “The way to do that is to brainstorm things about your relationship that may be unique to your love story.”

“Think about how you first met, how you fell in love, shared hobbies that brought you together, moments in your relationship that made you stronger, etc. Then circle those ideas that you think could be used as the central theme in your marriage proposal,” the proposal expert suggests.

Commenters thought that the situation was ridiculous: “The second one should have been it”

Image credits: throwra70ahhhh

The couple talked, but their solution surprised many people

Image credits: Alena Darmel/Pexels (not the actual photo)

Image credits: Andrea Piacquadio/Pexels (not the actual photo)

Commenters were skeptical about the couple’s future: “Wish you best of luck in your eventual divorce”

Image credits: throwra70ahhhh

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