How to Plan Your Wedding Proposal

From Runaway Bride  Courtesy of Paramount Pictures
From Runaway Bride (1999) Courtesy of Paramount Pictures

Whether the ring is already tucked away in a safe or you’re still flirting with the idea of popping the question, it’s never too early to start thinking about how to pull off your proposal plan without a hitch. Because social media has turned the business of proposals into displays of one-upmanship, the pressure to stage an elaborate scene is real—but it doesn’t have to be that way.

Here, the steps to run through when you’re thinking about how to propose.

Give yourself time to plan
After you get the ring, Glendeline Maduro, founder of The Proposal Planner Aruba, advises planning eight weeks in advance, give or take a few weeks depending on the grandeur of your scheme. Assuming you’ve broached the subject of spending the rest of your lives together in some capacity and share the same values, the proposal shouldn’t completely blindside your partner, but an element of surprise will add to the occasion's delight. Clear your web history and use your work email to make arrangements. Disable email previews on any shared devices so an accidental notification doesn't spoil the moment.

Location, location, location
Old wisdom suggests choosing the location of your first date or kiss. But Guerdy Abraira, lead event designer and owner of Ocean Flowers and Events, says to pick a new location. “It will set the tone for your engagement. Forget the past and create the future,” she says.

If your partner is on the shy side, keep it intimate. (Think of Prince Harry and Meghan Markle—he proposed during a cozy night in, over roast chicken!) If they tend to binge-watch elaborate flash mob proposals on YouTube and generally thrive in the spotlight, make it a family—or community—affair. For outdoor proposals, make sure you have a plan B if the weather doesn’t hold up or a permit on private property. Once you’ve secured the location, visit it a week or two beforehand during the same time of day on the same day of the week. Assess factors like traffic, walking distance, crowd size and lighting. Ensure there’s room for a photographer to hide should you choose to hire one. The only surprise on that day should be the proposal itself.

Keep your support system small
If your imminent proposal is completely dominating your thoughts, you might be tempted to unload on everyone from coworkers to bartenders. But the more people who know, the higher a chance someone will ruin the surprise, Maduro says.

Keep one or two best friends or a family member in the loop for logistical reasons (say, if you’ve enlisted them to photograph the moment, decorate the location, or slyly escort your soon-to-be betrothed to the scene). Otherwise, keep it a secret until you’re ready to go Instagram official.

Prepare bullet points
…But don’t write them down on your sweaty palm. There’s a stark difference between robotically reciting a scripted speech and having a few talking points in the back of your mind. While awkwardness is widely considered cute and quirky, you want to keep the stumbling to a minimum so as to get your point across.

“You should have an idea of what you’d like to say, which words you’d like to use or special moments you’d like to mention. By completely winging it, you’ll freeze up. Every second will feel like a minute,” Maduro says. But learning a speech by heart has its pitfalls—if you miss one word you might get lost and completely blank. Try to achieve a happy medium between improv and forethought.

Organize the whole day
Think of the proposal as one part of a monumental day. The rest of the afternoon or evening should be accounted for, Lobeto suggests—even if that means a quiet picnic for two, a couple’s massage, or a trip to the bedroom. Again, you know your partner best: A lavish catered brunch for the whole family post-proposal will either keep the exciting momentum going or completely overwhelm them.

If this list is stressing you out? Abandon the plan
Save the stress of planning for the wedding and opt instead for a spontaneous proposal, which Abraira recommends as more genuine and raw. You don’t want to begin resenting how many resources you’ve invested on a single moment and burn out before the big day. “Sometimes planning can get cumbersome and then it becomes not fun, which is why it’s great to hire a planner or get a friend to help, but if that fails, carpe diem.”