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Jackie shows off her ring

My first marriage proposal

So while we were in Puerto Rico earlier this month, a couple on my tour got engaged! I’m thrilled for Caleb and Jackie, and I’m delighted they had such a special moment on our trip.

I didn’t know at the time because they kept it a secret. They wanted to tell some people before others, and somehow I wasn’t at the top of their list. I don’t know how Jackie’s mother outranks me, their extra-special tour director…

Anyways, here’s how it went down. We had a free day on the island of Vieques, which has a number of great beaches. One morning, I dropped everyone off at the beach of their choice with a cooler of refreshments, then picked them back up that afternoon. Most of the group decided to go to the Playuela beach. But Caleb and Jackie chose Caracas beach instead and spent the day there together.

While they were there, Caleb surprised Jackie with a ring and a proposal! He’s a videographer, and he made a video recording of the whole thing. Jackie was flabbergasted, couldn’t believe it, but only needed a moment to get over the shock and say yes.

I picked them up that afternoon, never suspecting they had anything bigger on their minds than Caleb’s sunburn! (Unfortunately when he put on sunblock, he missed most of his back. It looked painful.) Here are a couple pictures I took later that day, which suddenly have more sentimental value than they used to. You’d never know something huge had just happened, right?

Caleb and Jackie at the fort-museum in Vieques

This is at the restored Spanish fort/prison that now houses the Vieques history museum and archives. After we got a presentation on the island’s history, we were helping close the place up. Caleb found out the hard way that the shutters are a little temperamental. But if I were 150+ years old, I’d probably be a little temperamental too.

Jackie and Caleb walk along a Vieques street

Walking back from the fort to our hotel.

Again, congrats to the happy couple!

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