How To Propose Marriage Without Screwing Up

How To Propose Marriage Without Screwing Up

A wedding proposal deserves a little spectacle. Not an obnoxious viral-video stunt, but something to make your partner feel special. Putting some planning into it is an act of love. I talked to January of Engaged by January, a proposal planning service, about what to do – and what not to do – when you propose. And it’s all advice you can use on your own.

Ask “What don’t you want?”

January says this might be the most important question you can ask: “That can really save you a lot of pain and suffering.” If you’re worried this will spoil the surprise element, then get backup:

Team up with their friends

Get a friend to bring it up in conversation; it’s not an unreasonable topic so you might even hold onto plausible deniability. Your mileage will vary here; by this point I knew my partner’s tastes more than her friends did. But if you need backup, ask for it.

Get the right engagement ring

January sees a lot of proposers go overboard on the ring. Instead, try to match your partner’s existing jewellery style. Look at what they wear to a special occasion. Check their Pinterest. Consider a gemstone other than a diamond.

If you’re using a family ring – from your side of the family – consider resetting it. If it’s from your partner’s side, play it safe, and wait until after the proposal to resize it. Either way, clean and polish it before the proposal.

If you want to pick a ring with your partner later, January strongly recommends proposing with a placeholder. “Don’t be empty handed.”

Ask on a weekend

“Don’t ask her on an evening when she has to work the next day,” says January. “I see this a lot. It will bone her whole week. Do it when you have some time to bask in it afterwards.”

And don’t integrate your workplace too much into this, even if that’s how you met. Don’t reference work in your proposal or in some engraving on the ring. “Jobs change. People get fired.” While January thinks a work function might be an ok site for a proposal, maybe you should avoid it.

Plan, plan, plan

Depending on your taste, your proposal can be a quiet and intimate event, or it can be more of a surprise party with a special guest. If it doesn’t ruin the intimacy, January recommends you plant a photographer to capture the moment.

If you’re low-key, you can simply plan a nice dinner afterward, inform the waitstaff that you’ll be freshly post-engagement, and get some discreet special treatment and champagne. (But make sure neither of you are starving or overly tipsy when you pop the question; you want to be in a pleasant and non-fainting mood.)

If you really want a spectacle, January suggests integrating the proposal into an activity you two do together: “One time I had a girl and her friends do an escape room on her birthday (she LOVES them) and had the escape room make the ring the end. It was awesome. Another time I knew a girl was obsessed with a certain band, so called up the band’s management and asked if they could help out, and he proposed on stage at the concert that she was at with her girl friends.”

Personally, this would be my nightmare! But that’s the point. The best proposal is the one that feels specific to you and your partner, so you can tell the story for years to friends who are secretly judging your choices because they’re jealous of your love.


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