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Should Your Proposal Be A Surprise?

As I finished reading the last line aloud I looked up and there he was, Jacob & Co. ring in hand, waiting for my answer. I threw my arms around him and continued to sniffle, choke, sniffle, choke.
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Should your proposal be a surprise?

Yes, even if it's only a part of it.

We were nearing our third year as a couple, yet we never once spoke about marriage or even about getting engaged. My boyfriend's reasoning: "What's the joy in a proposal without the element of surprise?" Then, one cold wintery day in December while we were shopping for Christmas presents, his eyes began to dart around the store while his weight shifted from one foot to the other. I knew something was up. The Starbucks coffee cup in his hand was shaking ever so slightly as he almost inaudibly whispered, "Say we were to be together forever." So far, so good: a hypothetical yet definitive statement. Yes, I nodded. Without looking into my eyes, he continued, "I would need to get you something to make it official. Well, the thing is ..." (he has a way of drawing out his sentences at times) I just don't know." Don't know what? I looked up, alarmed. "You have very particular tastes. Especially when it comes to style. What if I got you one that you hated?" His breath shortened, and a look of panic clouded over his eyes. The silence that followed was impenetrable. I was at a loss for words. Awkward? Completely.

"This is something you were supposed to ask my friends," I explained gently. Oh. "Especially since you wanted the entire thing to be a mystery and we've never really spoken about it. But I'll email you a photo of the exact ring I want and we'll never speak of this again." And we never did. I made clear where my heart was by clicking "send," and that was how our pre-proposal proposal ended.

Time: Two weeks before Valentine's Day. The boyfriend pipes up on a lazy Sunday, "I think we should get away. Let's be spontaneous. I was thinking the Adirondacks one weekend in March. The 16th to the 18th?" My, that's specific. Over the next two weeks, plans shifted to skiing at Stowe, Vermont, and then finally landed on a beach vacation in the Bahamas. There's nothing I love more than a good, old-fashioned surprise, but I had my suspicions that the proposal was upon us and so I played it out in my mind. The boyfriend is an extremely private person, so I knew it wouldn't be a showy public affair. It would go something like this: We'd arrive, he'd act nervous all day and then would ask me during or after dinner the first night against the backdrop of a sunset (cue the violins ... now). Perfect. We would spend the rest of the weekend basking in an engagement glow sipping mojitos and soaking up the sun.

I boarded the plane, expectations high. We checked into gorgeous and super-colorful Compass Point Beach in Nassau then headed straight for the beach. But not before I saw the dock. There was an above-the-water walkway that led straight to an open-air dock where staff members were preparing an al fresco dinner for two. That was it. This, I thought, was how he was going to propose.

But he made no mention of the dock and we decided on sushi and sake at Nobu in Atlantis. The next day, we took a local bus downtown and hopped on a ferry to Blue Lagoon where we swam with the dolphins. It's going to happen tonight, I kept telling myself. Dinner, he told me, was going to be at the dock. Yes! We toasted with a glass of white wine, watched the art of making a conch ceviche salad, and strolled down the walkway.

Fact: Photos of couples dining on a beach or on a dock are completely staged. During our meal, I walked to our room twice to pile on layers -- jackets and a scarf -- and had to hold down our tablecloth while the wind whipped my hair, blinding me, as I tried to butter my bread. If he was going to propose, he had best do it soon before we froze to death on the boardwalk. We passed on dessert and then he asked for the check. A dark cloud suddenly descended over me. Was it really not going to happen tonight? I tried to conceal my disappointment but failed miserably. He knew me too well.

We grabbed our glasses of wine and headed to our room. I had taken only two steps in when he grabbed my hand and said, "I have a gift for you." Be still, my heart. He dug into his duffel bag and grabbed a box wrapped in silver ribbon. It definitely wasn't a ring from the size of it. I sat down and carefully unwrapped it. Inside was a beautifully illustrated children's book detailing the ebbs and flows of our relationship in rhyme: how he brazenly approached me knowing full well that my now ex-boyfriend was at the same bar, our first trip, our silly shortcomings and inside jokes. It was brilliant; both witty and sentimental at the same time, it reminded me again exactly why I wanted to marry this man. As I finished reading the last line aloud, I looked up and there he was, Jacob & Co. ring in hand, waiting for my answer. I threw my arms around him and continued to sniffle, choke, sniffle, choke. "I'm confused -- is it a yes or a no?" he asked me. Yes! It's a yes.

Was I surprised? A little. I knew the question was coming but didn't know exactly when. We flew back to NYC and went to dinner to cap off our whirlwind weekend. When the server escorted us to the back of the restaurant, we approached two wooden doors that he pushed back ... slowly. I walked into a room with 16 of our best friends gathered around a table to celebrate our engagement. He had organized the entire event months in advance. My mouth dropped open, cartoon-like. I didn't know whether to laugh, to cry, or do both. This was a surprise -- and the best one at that.

Below, photos from our engagement trip: