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Proposal Pitfalls

Plan the perfect proposal — and avoid disaster.

Asking your beloved to marry you is momentous. With the trend toward elaborate proposals growing, the pressure is on to make it memorable, shareable and unique. But we’ve all seen the viral evidence of when proposals with perfect intentions go horribly wrong.

Don’t go empty-handed

Even if you don’t have the perfect engagement ring picked out, have something! Nothing says, “I really didn’t think about this” like popping the question with nothing to show for it. In a survey by The Knot, proposing without a ring was ranked as the No. 1 mistake when popping the question. If you don’t want to shop for a ring without her (and more than half of couples getting engaged select an engagement ring together), but still want to surprise her, many jewelers will let you buy a ring and exchange or upgrade later. A promise ring is also a sweet placeholder, or you can borrow an heirloom from your (or her) family.

Pick a safe place

Nerves can get the best of the most confident people, and rings are small and easy to fumble. A cautionary tale went viral when a perfectly planned proposal went “plop.” A romantic waterfront moment resulted in snorkel and scuba gear when the ring got dropped between the planking on a dock. The ring was recovered, she said “yes,” and it all worked out in the end, but not without a lot of stress and swimming. Other water hazards are capsizing boats or rogue waves slamming in at the wrong time.

Time it right

Resist the temptation to get swept away by the moment. You may suddenly feel like proposing at the stroke of midnight on New Year’s Eve or while slow dancing at your best friend’s wedding, especially if you’ve had a couple of celebratory drinks. Get a hold of yourself — this is not an impulsive matter. If it seems like a good idea the next day, get your plan together.

Restaurant do's and don’ts

Restaurants are perennially popular places to pop the question. Romantic dining spots are staffed by folks with experience at making proposals go smoothly. They strongly recommend against hiding the ring in a flute of champagne or in the dessert or other food — while the initial surprise looks great, fishing it out of glass or piece of cake is inelegant. And then it’s sticky. Avoid.

Time it right in the restaurant — wait until dessert. If the proposal comes with cocktails or appetizers, and the answer is “no,” you’ve got the awful choice of getting up and leaving or awkwardly sticking it out.

Keep it secret

Don’t be like the guy who was planning a flash-mob at a beach community and took his recruitment effort online to a popular message board. His soon-to-be fiancée logged on to do some vacation planning, recognized his username, put it all together and actually pretended to be surprised on the big day. After all, so many people were excited about participating, and it was still special. But it wasn’t a surprise.

So keep it off digital channels, and don’t confide in too many people — even face-to-face. An honest slip can happen, and you know some people just can’t keep a secret.

Make it private

We may have seen the wave of public performance art proposals crest. In surveys, most women say they don’t want a big scene in front of a crowd at a sporting event or even friends and family. If you’re not completely sure the answer will be “yes,” you risk heartbreak and humiliation in front of the person you love and a whole crowd.

Search YouTube for failed proposals if you need more proof. And prepare to cringe.

It’s got to be special

This is, of course, one of the most important things you’ll both do in your lifetimes — so while there are ways it can go south, it should still be special. This is a decision you make together, a commitment you make together, so make it about the two of you. Have the celebration with your friends and families later. Savor the moment and remember it as the start of something even better!

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