Marriage Proposals That Almost Went Terribly Wrong
And she still said yes!
The thing about proposals? Many of the best-planned ones are usually surprising by nature. And much like any surprise, the fun in it is the possibility for the unexpected. These engagement stories didn’t go exactly as planned. But the flaws, fumbles, and flops made them perfect anyway.
An Adorable Disaster of a Proposal
Nearly everything that could go wrong did go wrong when Foursquare founder Dennis Crowley popped the question to then-girlfriend, stylist Chelsa Skees—including a citywide blackout and a stubborn proposee. But what went right more than made up for the mishaps.
A Proposal (Involving an X-Acto Knife and a Fumble!) That Nearly Cost This Couple the Ring
Originally, this groom-to-be planned to propose by carving a ring-sized hole inside a notebook. When that didn’t work out, he nixed the idea to go a more traditional route—or so he thought.
A Proposal Almost Ruined by Two Guys Just Trying to Do Their Jobs
This graphic designer’s boyfriend had the perfect ploy in place: A romantic stroll in Madison Square Park—what could go wrong? But just before he could pop the question, security guards stepped in.
A Proposal With a Scheduling Conflict
The cameras were rolling when this retail merchandiser asked his girlfriend to marry him, following a carefully planned series of events through San Francisco’s Ferry Building. The only problem? “I had forgotten to tell Melissa to be free that day,” says her now-husband. “I had it on my calendar for at least two months, shared it with all my friends and her out-of-town family, but I didn’t tell Melissa!” The unknowing bride-to-be ended up booking herself for an all-day conference because of course she did, which Matthew didn’t find out about until a week before.
A Proposal With a Missing Ring
Tad Ro, now a chief digital officer, asked Annie Lee to marry him during a weekend getaway to the central California coast. “He gravitates to the unexpected,” says Annie, a product manager for the same startup, describing Tad’s surprise proposal on a white-sand beach. But on that day, Tad shocked even himself when he reached into his jacket pocket and came up empty-handed. “That’s when he realized that he had left the ring in the car,” Annie says. “He told me he was nervous that day and thought he had everything ready, which he did, but he forgot one shiny detail.”
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