We recently got a poignant letter from a man who thinks he had arranged the ideal, romcom-style proposal for his girlfriend Rachel. He expected things to go perfectly after months of saving for the ring and planning the big day. Instead, his dream proposal took an unexpected twist. A combination of ring disagreements and some unanticipated interpersonal troubles resulted in a reaction he never imagined. He is now reaching our readers for guidance on what to do next.

Our reader planned a dream proposal for his GF: renting a yacht and choosing the perfect ring.
“I am 28 years old and recently proposed to Rachel, my three-year girlfriend. For six months, I gave it my all to organize the perfect proposal since I knew how important it was to her. Rachel is a tremendous romantic—she loves romcoms—and I wanted to give her a moment that felt as beautiful as the movies she loves. I spent hours going over the minutiae, attempting to make it as unique as possible.”

“I also spent a lot of time looking for the perfect engagement ring. I know how important it is to her, and I wanted to purchase her something wonderful. Finally, I purchased a gorgeous 1-carat engagement ring for $5,000 because I’m saving for a house. I figured she’d appreciate the gesture.”

“For the proposal, I recreated the lunch she prepared for me on our third date, which was a significant memory for both of us. And, because she is a major fan of the 1980s film Overboard, I leased a yacht to make it feel like something out of the movie. I was confident it would be a proposal she’d never forget, the kind of story we’d remember for years.”

But what he thought would be a beautiful moment turned into a complete disaster.
“My girlfriend did not like it. For the record. I am just a normal man who works in construction. I don’t have a lot of money to throw around, but I assumed we were on the same page: saving for a house so we could start a family. I’ve managed to accumulate around $80,000, and I thought that was where we should focus.”
“To me, a home is more important in the long run than a flashy ring. But Rachel had other ideas. She complained that the diamond was too tiny. She agreed to accept my proposal if I gave her a different ring.”

“I agreed. But when I told her I had $80,000 in savings, she was furious that I hadn’t spent the entire amount on the ring. She accused me of not loving her. But I still don’t believe the ring is that important compared to living together in a wonderful house.”

The couple couldn’t agree on the price of a new ring.
“She showed me rings she loved, but they were all much out of my price range. We began to argue since everything she wanted was much beyond the budget I had stated at the outset. She even suggested that I obtain a side job to save additional money for the ring.”

“Again, I’m not against purchasing her a prettier ring, but we couldn’t agree on a price. It felt like we were on opposite sides of what was essential.”

“Then there was the proposal itself. I thought I was being quite kind when I recreated our particular experience and rented a yacht. However, that was not what she had in mind. She later told me that she had always wanted to make a big, flashy proposal.”

So, our reader started to plan Proposal 2.0.
“I spent $70,000 on her new ring, wiping out a large portion of my money. I leased a modest restaurant, invited her family and friends, and went all out in public. She finally said yes, and for a few minutes, it felt like the joyful conclusion we both desired.”

“But then she started acting aloof, and I couldn’t shake the sensation that she was beginning to resent me for not being able to provide her with the beautiful, lavish life she always seemed to desire. No matter how hard I worked or how much effort I made to make things unique for her, it never seemed to be sufficient. I understand—I’m just a regular person, a construction worker. I’m not bringing in huge money, but I’ve always done my best to be there for her, to build a future together.”

“Then, after two years of marriage, during one of our routine disagreements about money, she said something that hit me like a ton of bricks. She said, ‘I made a mistake by picking you over Jeremy.’ It seemed as if everything just clicked. I had no idea who Jeremy was until that point, but then everything began to make sense.”

“It turns out that her former university mate, Jeremy, had expressed interest in her when we first met. She had never mentioned him in any major way before, but in that moment, I felt as if she had been comparing me to him all along. According to what I’ve learned, Jeremy had more money than I did, and he could’ve probably given her the life she seems to want.”

“What she said cut hard. It made me feel as if all of my efforts and sacrifices to make a life together had been for naught. I felt like I was just the second option she went with because I was the only one willing to offer her my heart at the time.”

“I’ve always tried my best to provide for us. I might not be making a lot of money, but I’ve worked hard, saved for a house, and attempted to provide a secure life for us. But now it feels as if none of that mattered since, deep down, she may have always desired the kind of life Jeremy might have provided her.”

“Since that battle, I haven’t stopped thinking about it. It’s like a dark cloud is hanging over our marriage. I keep wondering if she regrets selecting me, and I know that no matter what I do, I will never be enough for her. It’s been difficult to keep going with this doubt hanging over me every day.”

“I really thought we were building something real together, but now I’m left questioning if I was ever enough for her. And that hurts more than anything.”