Man Proposes to Fiancée Twice, Second Time Even Better

After an imperfect first proposal, he planned a magical second one at Disneyland.

Published on Feb. 14, 2026

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A man decided to propose to his fiancée a second time, about two years after the first proposal, because the initial engagement day was marred by stressors and unsupportive connections. For the second proposal, he planned a special day at Disneyland, where he got down on one knee and renewed his commitment to her, and she said yes again. The couple now has even more wonderful memories to reflect on, and the man recommends a second proposal to anyone who felt their first attempt wasn't as magical as they deserved.

Why it matters

This story highlights how a couple can choose to have a second, more meaningful proposal when the first one didn't quite meet their expectations. It shows that traditions can be broken, and a couple can create their own special moments that are entirely focused on their love and commitment to each other.

The details

After the first proposal in New York City, the man felt that certain aspects of the engagement didn't quite meet his and his fiancée's expectations. There were people in their lives who were emotionally standing in their way instead of celebrating them, and the man was also at the pinnacle of his unhealthiest self, both mentally and physically. Seeing the pain behind his eyes while looking at the photographs from that day became too much to bear. So, about two years later, the man planned a second proposal during a Disneyland trip, where he got down on one knee and renewed his commitment to his fiancée, surprising her with a matching piece of jewelry. They then had a vegan meal surrounded by Disney characters, creating a magical moment that was entirely about their love.

  • The first proposal happened in New York City.
  • The second proposal took place about two years after the first, during a Disneyland trip.

The players

Jamie Evan Bichelman

The man who proposed to his fiancée twice.

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What they’re saying

“I felt inspired as I planned another proposal to my fiancée.”

— Jamie Evan Bichelman (businessinsider.com)

“Now, we have even more wonderful memories to reflect on, and the best part is, the day was entirely about us and our love.”

— Jamie Evan Bichelman (businessinsider.com)

What’s next

The couple is now planning their wedding, which they hope will be as magical as their second proposal.

The takeaway

This story shows that a second proposal can be a meaningful way for a couple to create a special moment that is entirely focused on their love and commitment to each other, even if the first proposal didn't go as planned. It's a reminder that traditions can be broken, and couples can choose to celebrate their relationship in their own unique way.