5 Secrets of a Perfect Proposal

5 Secrets of a Perfect Proposal

Guys, popping the question is all about making it personal
James Allen engagement rings, james allen rings

By Taylor Davies | Last Updated: Sep 21 2017 | 7 min read

James AllenA weeklong series dedicated to everything guys need to know about getting engaged, from picking the perfect ring to planning the perfect proposal.


“Will you marry me?” These four little words are some of the most important ones you’ll ever say. They’re right up there with those other two tiny-yet-monumental words, “I do.”

this doesn’t look like a proposal, but trust us, it is (and it’s sooo romantic)

That’s right—your favorite perpetually single SG editor is here today to talk about popping the question! While I don’t have a serious beau in my life at the moment, I’m still a woman. As such, I have absolutely envisioned the perfect proposal (and the perfect ring) with a rotating roster of Mr. Right’s throughout my life.

So if you’re in a happy, sexy, fulfilling, inspiring relationship that seems like it might be “it,” there’s a 278% chance the woman you’re in it with has listened to you talk about – oh, I don’t know – how you want waffles for breakfast, while imagining what it would be like if you asked her to have waffles with you every day for the rest of your lives.

Meaning? For better or for worse (sorry, I couldn’t resist), this moment really is about her, if only because she’s spent so much time thinking about it. And listen, I know that puts a lot of pressure on you. You want her to be happy. You want her to remember it forever. You want her to say yes! And of course, you want to nail the ring. That’s why I’ve gathered you, dearly beloved readers, here today.

Along with the experts at JamesAllen.com, the fastest growing online retailer for diamonds and engagement rings, I’m going to help you zero in on how to plan a romantic, fantastic, “story for the grandkids”-level perfect proposal that you’ll both treasure forever. Below, five things to keep in mind once you know she’s the one.

1. Observe how she talks about others’ proposal stories and engagement rings.

Here’s a moment where doing some “active listening” will pay off dividends (I know it’s kind of a hokey term, but trust me—it works!). Pay attention to her inflection as she describes how it went down: where they were, if anyone else was there, and of course, what the ring looked like and how she felt about it.

If you can hear the sarcasm dripping from her voice as she describes how her cousin’s boyfriend paid a skywriter to etch “Will you marry me?” in the clouds, for example, she probably doesn’t want an elaborate production for all the world to see. If she gushes over the moment her newly engaged work friend’s family jumped out of the bushes to surprise her, you can bet she’d love to celebrate with loved ones soon after the moment.

Note especially how she describes the ring! Did she sound swoony over her cousin’s stunning solitaire? Or wink at you a little bit when she mentioned how much her friend’s three-stone ring glittered in the sun? Those are the “hint hint” moments you’ll want to remember later.

And not for nothing: she’s probably sharing these stories and elaborate ring descriptions with the express purpose of telling-but-not-telling-you what she would want when it’s her turn. (See what I mean about that whole active listening thing? We’re clever like that.)

2. Don’t be afraid to ask for help.

Worried about “asking for directions” on this? Don’t be! It’s 2017 and no man is an island! Asking for help is awesome and seeking advice is, well, just plain smart. It’s why you’re reading this, is it not?

Of course, you’ll want to be stealth about it (you don’t want to blow your cover, after all), but go ahead and lean on your friends and family as you plan your perfect proposal. Her sister might know her ring size; maybe your coworker hides the ring for a week or two; let her bestie deliver her to the scene of the proposal. You’ll still get all the credit, but trust me, both your hearts will swell with the feelings of support and love from the people around you who helped pull off this special moment.

If bringing in too many friends or family members feels risky or not your style, deploy experts to your advantage. From loose diamond research to ring shopping to engagement story inspiration, JamesAllen.com has a ton of resources for grooms (and brides!)-to-be looking for guidance. Plus, you can call or text their experts 24/7 (don’t worry, they’re not working on commission so you know you can trust ‘em), which is sort of like having a personal engagement expert in your back pocket.

3. Make it personal, not perfect.

Asking the love of your life to marry you is a big, emotional occasion, and there’s a lot of pressure to make the moment “perfect.” But listen up! I’m here to tell you that if your proposal is thoughtful, spoken from the heart, and done in a way that feels true to who you two are as a couple, she will love it. She will gush to her friends about it. She will cry. You will probably cry. I’ll probably cry when you comment on this post a few months from now to tell me how it went.

So where do you begin when planning a personal and meaningful proposal? Obviously, it starts with the ring! Peek in her jewelry box while she’s out at a spin class for intel on her style. Ask her best friends for their advice, too. Or consider shopping for the ring together! Sharing this part of your marriage journey (and guaranteeing she really, really loves the ring) won’t diminish how special and surprising the actual proposal will be.

Next, think about the places that have been important to you as a couple, since landing on a location another big decision. Maybe you guys just bought a house, so the living room is now your favorite place on earth. Maybe you both love to sail, so a night at sea is just the ticket. Maybe you two had your first Tinder date at a funky coffee shop in Brooklyn, and returning to that fateful meeting spot feels apropos.

Finally, remember that what she’s saying yes to is you, not the proposal, so doing something that fits you both as a couple is all that matters.

4. Have a (flexible) plan.

Once you’ve landed on your ideal setting in which to pop the question and thought about what you’ll say, it’s time to make a plan. Pick a day and set things in motion. Then? Prepare to adjust. The universe has a funny way of conjuring up superstorms, canceled flights, dead batteries, lost luggage, flat tires and forgotten everythings—right when it’s the least convenient.

Meaning? Be prepared for something to go wrong in your flawless plan. Maintaining your cool and being able to laugh when the doves won’t fly out of that cage at just the right moment or the words-on-cupcakes you ordered say, “WILL YOU MERRY MEAT?” is all you can do. 

5. Literally, truly, and actually get down on one knee.

I’m not going to tell you what to say or how to say it. When the moment arrives and you’re ready to propose to this amazing woman, all you have to do is speak from the heart and those will be the right words.

However! I am going to use this platform to push a personal belief, which is this: Getting down on one knee when you propose marriage is a hugely important gesture. Unless you have a medical condition which prevents you from doing so safely… I say, to the floor you go! This traditional posture (which dates back to the 19th century) began as a sign of loyalty and surrender but now is just, well, romantic as hell.

What I’m getting at here is that the key to a perfect proposal is simple: Make it memorable and personal, in whatever way feels right for you as a couple. Whether you make an elaborate plan or embrace the spontaneity of a moment too good to pass up, if you look her in the eyes and mean what you say, it’ll be fantastic and special and most importantly, she’ll say, “Yes!”



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Taylor Davies splits her time between NYC and Sun Valley. She loves writing about menswear, overpriced martinis in dimly lit hotel bars, and cross-country skiing. Not necessarily in that order.