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How to Plan the Perfect Proposal—So She Says 'Yes'

Five basic tips to make sure you get it right the first time.
How to Plan the Perfect Proposal—So She Says 'Yes'

Getting engaged is one of the most monumental decisions you’re going to make in your lifetime. It falls in line with buying a house and having kids or conversely, becoming an excursionist or a high-flying careerist. Bottom line: a lot can go wrong. A proposal can crumble or it can serve as the cornerstone of life-long marital bliss. To ensure it’s the latter, make sure you abide by some basics. 

New York City-based portrait photographer Carl Chisolm has been capturing couples’ engagements for about two years—under the radar, of course. Hiding in the backdrop, summoned only by the drop of a knee, Chisolm says he serves as a “set of eyes, a point of memory for the couple,” swooping in at just the right moment to capture the tears, the smiles, and the ‘I do.’ 

Here, Chisolm offers a blueprint—some dos and don’ts for proposing to your significant other. Listen to the guy; not just because he’s married, but because he’s never seen a proposal go awry. He’s never witnessed a ‘no.’ 

Follow these tips and you’ll have smooth sailing all the way to the altar.  

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If you’re going to propose in a restaurant, a bar, a hotel (basically any venue), Chisolm suggests doing a site visit at least a day or up to a week before. Speak with the manager or the head of wait staff so they have a heads up, they know the gist of your plan, and they can react accordingly. Obviously you don’t want your waiter dropping hints left and right, lingering around the table, giving you a nudge of an elbow and a wink goodbye, wishing you good luck on this most special of occasions.

This could also be a great chance to coordinate any specific plans, say if you want your waiter to stay clear of the table after dessert; if you want to arrange a private room for just the two of you; if any special details like candles, lights or decorations can be added. Put thought into the details without going over the top.

“I think the best proposals are just really simple and true to that couple; it’s not something that’s out of their normal routine,” Chisolm says. “Original is great, but original can also be kitschy and cheesy. It depends. I would never advise anyone to do something extravagant like rent a helicopter for the day.” 

Read: special and memorable doesn’t always mean extravagant. Chisolm photographed a proposal at the New York Palace Hotel’s plaza; the couple had made it a tradition of going there every Friday for drinks. So, the boyfriend made their favorite spot even more beloved by proposing to his girlfriend in the courtyard. Chisolm recalls another man proposing to his girlfriend at Dos Caminos restaurant on Park Avenue; again, it’s what the location means to you as a couple not just the fact that it’s a place with terrific atmosphere, or knockout margaritas and guacamole. 

The bride-to-be didn’t even notice Chisolm snapping photos of them just two feet away. “When the moment’s right, it’s like nothing else in the world matters,” Chisolm says. “What’s really needed is an expression of the love you have for each other.” 

Chisolm says it’s best when the activity or atmosphere feels authentic and natural, but that’s easier said than done since you’ll presumably be nervous, anxious, frenetic and any other variation of the emotion. Treat the big night like any other date or any other time you’ve been together, he says.

Make sure you’re wearing a good amount of deodorant, he adds. “I’ve shot a lot of sweaty guys and done a lot of sweat re-touching.” Have a cool drink in hand, and take a sip of it before you pop the question. Also, don’t stand up too fast. Passing out will definitely put a damper on the evening.

If you want to think outside of the box a bit, say by enlisting a flash mob to help along with the proposal, then make sure it’s not a bunch of strangers. “Don’t have too much trickery,” Chisolm advises. “But do have an element of surprise.” Invite all your family and friends if you want to do something unexpected, so she’ll get the surprise of her life and get to share it with everyone she loves. 

“A friend of mine shoots a ton of weddings and you see this a bunch of times—the guy having the ring put in champagne,” Chisolm said. “So this guy did that, only the waiter took it to the wrong table. It made for a pretty awkward 10-15 minutes.”

Don’t be this guy. In fact, avoid placing the ring in foods and drinks altogether. You don’t want the night to me memorable because you had to give your girlfriend the Heimlich.  

Good luck out there. 


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