What I Learned Proposing 30 Times

...in 20 months

I knew I wanted to marry Skully approximately thirty minutes into our second date during a drive up the South Florida coast. We were trying to see how far north on A1A we could travel and still see the ocean. The Hitchhiker’s Guide to the Galaxy radio play played in the background as we chased the nighttime ocean breezes in his black Mini Cooper. He waxed poetic about something that I disagreed with (I don’t remember what), and I thought to myself, “I think I could disagree with him for the rest of my life.” I didn’t propose that night, but I knew I wanted to. Somewhere near West Palm Beach, I started planning the first (of many) proposals.

A few months later, I sat Skully down and began what we eventually called marriage negotiations. Neither of us believed in surprise proposing (and I hate surprises in general). One of the feminist hills I’m willing to die on is that both people decide to get married, AND THEN one or both makes a formal proposal. Luckily, he felt the same way. Just another reason why I wanted to marry him in the first place.

Getting to Thirty

I always wanted to propose, but he also wanted a proposal opportunity of his own. He had some very specific ideas about what a proposal should look like. I had been a reader of APW for almost six years at this point, so I had some IDEAS about proposals and wanted to do… all of them. During those discussions of whether, how, and when we wanted to get married, I suggested the idea of doing thirty proposals. I mean, if one proposal was good, then thirty was better.

So that’s what we did. Thirty proposals (at least) given and received over the course of twenty months. It went down as one of the most fun parts of our engagement. No, we did not have thirty elaborate proposals during our engagement (we were paying for a wedding after all). Most were pretty small and insignificant to all but the two of us. They were everyday moments that solidified how much we wanted to get married.

It started with two

I ended up proposing twice in thirty minutes the first time. His ring arrived in the mail that day so I plopped next to him on the couch held out the ring and excitedly said, “Wanna marry me?” Y’all. Apparently feminist men being proposed to have very strong opinions about how said proposal should go down. Which is to say that he was not having my casual “Let’s do this!” proposal. He pointed out that we had a perfectly good balcony; that a glorious Miami sunset was minutes away; and that assuming he didn’t want romance was sexist. So we gathered on his balcony at sunset. I got down on one knee, pulled the ring out of a tin of his favorite candy, and asked him to marry me. He cried and said yes. Whew! Only twenty-eight proposals to go!

For the next several months, we proposed to each other in ways big and small. I hadn’t yet decided on what kind of engagement ring I wanted, so his proposals to me were often ring-less. He, however, ended up with a total of four (FOUR!) engagement rings. Each requiring a separate proposal (or two) of their own: in the frozen pizza aisle of Publix, the first time he met my family, sitting on the beach underneath the stars, while watching the sunset on the California coast. We proposed nine times during our first cross-country road trip.

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We proposed to each other every time we realized how profoundly our lives were about to change. When I had to explain how stopping at gas stations in rural areas at night was a no go, he made sure the gas tank never got below half full the rest of the trip. So I asked him to marry me. The first time we got the PCS (permanent change of station) transfer list, we realized that being a military family meant I would change careers often. He asked me again to marry him. He told me once that if any of his family ever said something racist while we were with them, we could leave then and there, never to return. When I knew he’d always have my back, I asked him to marry me.

Our proposals were a kind of short hand. I love you. I see you. I appreciate you. I am here for you. All these sentiments wrapped up in three little words, “Wanna get married?” It’s a promise we keep making to each other over and over.

One Christmas morning, I woke up to a small box under the Christmas tree. It was finally time for my big proposal with the engagement ring I knew he’d had in his closet for a week. I hastily unwrapped the box to find… a small tree topper. He asked me to put it on the tree. I stood on a stool and caught a hint of sparkle. My engagement ring dangled from the top of the tree. When I turned around, he was on one knee asking me to marry him.

The ultimate Proposal

For our negaversary we decided to go all out with a proposal for the ages. We planned our wedding to fall on the same week as our birthdays so that every year we’d celebrate a birthaversary week. That year we vacationed at a fancy hotel. We each called the hotel to let them know that we were celebrating the other’s birthday but also wanted to do a surprise proposal at dinner. I worked in luxury hospitality for years; we lived for excuses to stage elaborate double proposals in the middle of the hotel dining room. (Fact: Everyone loves other people’s proposals.)

At different intervals during the evening we snuck off to give the maître d’ our engagement rings. To be honest, had this proposal been a surprise, the entire staff would have given it away with the sheer amount of joyful giggling alone. Neither of us had any idea when the rings would arrive so we watched our drinks and food carefully, not wanting to choke on an unsuspecting piece of metal. Just before dessert, a pair of waiters carried huge glass cloches to the table. The cloche lids were pulled off in a cloud of smoke, a pile of pink rose petals spilling everywhere. Buried beneath the heap of rose petals sat two ring boxes. We pulled out the rings, got down on one knee together and proposed at the same time. And although we both knew exactly what was happening—although we had already proposed to each other at least a dozen times before—it felt just as romantic, surprising, and full of emotion as the very first time. We both got teary. Later that night we shared a champagne toast with Forest Whitaker. Because if Forest Whitaker offers you a toast, you let him.

Proposing after marriage

Since our wedding, we have continued the tradition of proposing to each other at regular intervals. Some people renew their vows every ten years. We propose to one another every other week. Every Marriage Summit, every anniversary, when we’ve made up after a fight, on cold Sunday mornings while we’re snuggled up in bed, and for no reason at all. There was even a proposal in Lover’s Lane at the Anne of Green Gables house (as one does). It’s our way of reconnecting with the heady feeling of being deeply and utterly newly in love. It’s a promise to keep going for as long as our strength will bear us.

What we learned in this exercise in proposing was that it is important—in big ways and small—to remember why you wanted to get married. Proposing to the same person, year after year, time after time, may seem like an eccentric waste of energy to some. But for us, it’s a way to keep reminding us that the core of our marriage is two people making a promise to each other to give love their best effort.


So for those of you who are stuck on proposal ideas, don’t be. Propose whichever way makes sense to you. And if all the ways make sense to you, do that. For those of you already married, keep proposing to your loved one. Remind them that if you were given a time machine, you’d still get down on one knee and start the crazy ride all over again.

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