Andrew Tolve tries to propose to his girlfriend. He fails spectacularly.
Looking back it seems almost comical, like we were unwitting actors in a Hollywood spoof. Cue the flock of sheep breaking free of their fence by the creek, then the kids on the 4×4 with the pellet guns, then the amnesia and speech loss.
In the moment, though, as I bent down on one knee to propose to the love of my life, it seemed like anything but slapstick comedy. In fact, it was devastating. I felt nauseous. And I was embarrassed—for myself, and for Ali, my girlfriend of more than five years.
The ring in my hand was a blue sapphire haloed in diamonds that I’d been trying to give her for weeks. First, I arranged a picnic in a local park only to decide at the critical moment the setting was too casual.
I began to look into exotic alternatives (a get-away to the Caribbean, a vacation to Napa) as Ali grew increasingly suspicious. Who could blame her? I was throwing away bank statements and changing passwords on Mint.com. I wouldn’t let her touch my laundry (the ring was hidden in the back of my dresser) or use my phone (it contained texts from her girlfriends who had helped design the ring).
With panic setting in, I booked a trip to north Georgia’s wine country, which only heightened her suspicions. I never planned our trips or picked out our restaurants, so why was I suddenly so eager to get involved?
She knew. I knew she knew. She knew I knew she knew.
We went anyway, both trying to act like it was spontaneous and exciting when really it felt like we were back on our first date, awkwardly avoiding our main purpose.
The first winery we visited was celebrating a Malbec release with a live bluegrass band, sausages on the grill, and lots of Malbec—great for a party, bad for a proposal. We tried to have fun, but I was distant and Ali was anxious.
The second vineyard was more intimate. Dogwoods and wild flowers painted the hills, and a lovely creek split the valley floor. Unfortunately, our “private” tour included eight middle-aged winos who, though harmless, weren’t the ideal backdrop for a proposal.
After the tour I led Ali over to the barn hoping for some privacy. As I took her hand, a few hungry sheep broke free of their pen. One lamb got stuck in the electric fence. “You have to get someone,” Ali said. “Hurry!”
I ran over to the barn and told a young farmer working on his truck about the situation. “I’ll be right over,” he said.
Back in the car, my head was spinning. Our next destination was a local creamery, and after that the inn for dinner, and after that bed, and if I didn’t propose then, when was I going to do it?
“Where are you going?” Ali asked me.
“Just to this bridge,” I said.
“Will you just follow me?”
She had a sick look on her face. I parked and led her down to the creek’s edge. “Ali, you know that I love you,” I said. “I really… ”
The rumble of a diesel engine interrupted. The vintner’s twin boys, who we’d learned had a fondness for 4x4s and pellet guns, were headed straight for us. “Oh dear god,” Ali groaned.
The boys cruised by, carrying on wildly. Once they were gone I tried again. “I really love you,” I mumbled. My eloquence had been reduced to that: I really love you. Her face was blanched. Mine was quivering as I began to fumble in my pocket and get down on one knee.
Again the twins came barreling through the field. This time they stopped on the bridge overhead and asked suspiciously, “Whatchya doin’?”
Ali said something but I heard nothing. I knew it was over. “Let’s get back in the car,” I said once they were gone.
“What were you going to ask me?” she said.
We drove back to the inn as if we were on our way to a funeral. She knew what had happened, and I knew what had happened, and we were both devastated that what was supposed to feel so right and exciting had instead felt so weird and wrong. Can a good marriage begin with a bad proposal? And could she ever accept the ring after this? Maybe it was a sign we shouldn’t get married at all?
That state of mind would thankfully pass. In the days that followed, I was reminded of how strong our love is. Ali and I had been dating for more than five years and had lived on three continents. We’d shared homes, parasites, bank accounts, aspirations, and setbacks. If we could survive all of that, we could certainly survive a hapless marriage proposal by a creek.
I also realized that I hadn’t really thought about why I was proposing in the first place. We had been so committed for so long, it was unclear what it meant to change our relationship status. Was engagement merely something we were supposed to do? If so, for whom? And why? Those are questions I’m still grappling with and that I intend to explore in this column.
What does it mean for a man to propose? How does it challenge him to be a better person, a better man? And, ultimately, how does he get it right, both the responsibilities behind the proposal and the act of doing it? I’m eager to hear your stories (the good, the bad, the indescribably ugly), as well as to share some of mine.
Fortunately, my second stab at it went better than my first. The Monday after we returned from the mountains, I filled our apartment with Tulips and candles and prepared champagne on ice, a filet mignon dinner in the works, and a five-page letter on the doorstep.
Inside I explained how, in searching for the perfect proposal, I had realized that no one moment could encapsulate all my feelings for Ali. Thus I planned to propose every day over the course of the coming year, to remind her why I loved her and wanted her to be my wife.
That, too, will be a part of this column, chronicling my 365 proposals and the lessons learned from them. For now, suffice it to say she accepted my first.
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