I proposed to my fiancée twice. The second yes felt even better than the first.
Business Insider
February 14, 2026
AI-Generated Deep Dive Summary
Proposing to his fiancée twice was a journey that Jamie Evan Bichelman describes as deeply meaningful. After saying yes on their first engagement, he felt compelled to propose again two years later when they had overcome past stressors and he was in a healthier mental and physical state. The second proposal, set against the magical backdrop of Disneyland, turned out to be even more special than the first.
The first proposal, held in New York City, had many positive elements—such as a beautiful ring and live violin music—but was overshadowed by external stressors, including unsupportive family members and Bichelman’s own unhealthiness at the time. Looking back at photos from the day, he noticed the pain behind his eyes, which made him realize they deserved another chance to celebrate their love without distractions.
For the second proposal, Bichelman focused on creating a memorable experience that reflected their growth as a couple. Instead of reusing the same location or repeating past mistakes, he planned an unforgettable day at Disneyland, complete with a surprise vegan meal surrounded by Disney characters and a touching renewal of his wedding promises. His fiancée’s blissful reaction made him realize that a second proposal could be a powerful way to recommit and create lasting memories.
Bichelman argues that proposing twice isn’t just unconventional—it can also be a romantic and innovative approach to expressing love. Whether it’s due to past mistakes, missed opportunities, or simply wanting to create even more special moments, a second proposal can remind your partner of your undying commitment.
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Originally published on Business Insider on 2/14/2026