How to Not Screw Up Your Marriage Proposal, Romeo
Illustration: Olivia Fields

How to Not Screw Up Your Marriage Proposal, Romeo

It’s only one of the biggest moments of your life. No pressure!

I didn’t enter 2020 anticipating marriage. And yet here we are. Over the holidays, in a tiny period of respite between election shenanigans and a terrorist attack on the U.S. Capitol, I tied the knot with my betrothed. (Yes, something good happened during 2020!) Now I go around saying “Ize married now!” and wiggling my ring finger approximately six feet away from the face of anyone who will entertain me.

You might be right behind me. But if you’re ready to tie the knot, take the plunge, jump the broom, or any other euphemism for getting married, you’ve first gotta nail the proposal. It’s a custom that dates at least as far back as the Roman Empire, when men would put two rings on it before marriage — a gold one for out in the world, and an iron ring to wear at home while doing chores. (SMH.) Diamonds entered the tradition once they became more readily affordable, and marketers made them ubiquitous beginning in the 1940s.

No one wants to go through an elaborate speech surrounded by loved ones just to see their partner wincing with clenched teeth — or get curved on a Jumbotron screen.

The engagement ring is only part of the deal, though. A proposal is about the full package and presentation. If you want it to be one to remember (for good reasons!), you wanna take the appropriate measures beforehand. For one, it’s best that you make sure your partner is on the same page before you start planning to get down on bended knee like Wanye and them. Use your words. Talk about the prospect of spending your lives together. Make sure they aren’t secretly planning on breaking up with you in, like, three weeks. No one wants to go through an elaborate speech surrounded by loved ones just to see their partner wincing with clenched teeth — or get curved on a Jumbotron screen.

Once you’ve got an idea of your partner’s readiness for forever with you, it’s time to make it an unforgettable moment. Here’s a handy checklist to consult before asking to take her hand.

Ring the alarm

The idea of a ring on the left hand is set in stone — but it doesn’t have to be a diamond. Ask questions to find out if your partner prefers a birthstone or something else entirely. These days, there are countless options for customizable rings. I asked my partner if I could have a four-finger gold name ring instead of a traditional ring. He said no. But he picked out a lovely pink stone. (I’m still getting that name ring, though!) Unsure of your partner’s ring size? Find a size chart, cut it to fit, and slip it on your partner’s finger while they’re sleeping to see the size. If you can’t pull that off, just eyeball it and get it sized to fit later.

Don’t fall for the parent trap

There was a time when it was expected that you’d ask your fiancée’s parents — particularly their father — for their child’s hand in marriage. It’s not necessary in modern times, but it doesn’t hurt to let their folks know what you’re planning. Since you’ll be combining families, it could be a nice gesture. Make sure you’re clear on your fiancée’s relationship with the parents. (If you’ve never met them or if they’re estranged, you can skip this step.)

Consider the kids

If your partner has children from a previous relationship, it’s essential to share your plans with them first — you’ll be their legal guardian once you get married, after all. When I found out my partner had gotten help from my 13-year-old with picking out my ring, I had all the feels.

Know when less is more

Keep your proposal classy, short, and simple. No trivia contests or treasure hunts that snake around your home — this isn’t a Case music video. If you want a few people to be there, invite some friends and family to dinner (masks up!) and propose as part of a toast. If you know your lover is all about the big display, go for it. Not sure? Err on the side of caution and keep it intimate.

Make it IG friendly

Let’s face it: These days, if it’s not on social media, it didn’t happen. Your partner may not be big on public announcements, but if you know your fiancée is going to drop that “I said yes” post on Instagram, make it fun. Go ahead and get that banner, bouquet of flowers and balloons, or a special IG setup that makes it feel like a moment. It can even be as simple as a Zoom background with a picture of the two of you. Say cheese, you crazy kids. Wait till you see how fun wedding planning is during a pandemic!