Planning for the day you propose to your future wife begins in about 6th grade. It did for me anyway. Then, and moving through junior and senior high school, ways to pop the question came and went.

There was the arena proposal during a major sporting event. Then it was a message on a blimp. Too rich. Billboard. Much more doable. Too cheesy. There was the on-air proposal idea, but soon after joining the TV News ranks you learn that is the quickest way to blow up your TV News career. People want news, not your sobbing girlfriend on the air. I digress. The clever ‘flash mob’ ideas came and went. Too much room for error. I gave up on the ideas for about a decade and then starting coming up with new ones.


This was the place, the iconic Moorings dock. Simple, but lovely.

Fast forward to now (yes, I know IT WAS ABOUT TIME!).  It finally hit me that this was the time. I needed a plan. I knew the spot. Islamorada in the Florida Keys. After spending years in TV News and moving from city to city while running a side business, a failed startup, video projects and other failed entrepreneurial ideas…I was stressed and tired out. I needed to relax. One day we took a trip to Islamorada and stayed at Cheeca Lodge. I remember that Saturday waking up and hitting the beach. It hit me. I had relaxed for the first time in years. We stayed another day and forgot about everything.

So I had my location. The plan would be simple. A dock proposal since Tara always wanted to be proposed to on a dock. I think it dates back to when she watched Dawson’s Creek. Something about that rings a bell, you’ll have to ask her. Regardless, it’s Florida, it’s paradise, there’s a dock…but as nice as the Cheeca Lodge dock is, I wanted it more quaint. The Moorings next door was the place that fit the bill (after a very high recommendation from a guy I played golf with months before).


The Orchid House. Our home for two, fabulous days.

We stayed at Cheeca Lodge the first night. We loved the room so much, I was bummed we had to move venues. I knew Tara was suspecting something because she always is. She’s a better reporter than most reporters. So it’s hard to trick her. But she went with the flow.

We moved into our house at The Moorings. It was awesome. I had pre-arranged a bottle of champagne to be set out on the dock ahead of time. The plan was to go to have a drink at a beach bar, come back to the dock and have champagne and then head out for a ‘bunch of activities’ including a special dinner across the street. I sold this story to her best I could.

In reality, the plan was to hide the ring in my pocket, have the champagne and I had pre-arranged a server to come out on the dock with a bottle of water and two glasses. She did. We both looked surprised. She asked:

Did someone spill their water?


The water Josh spilled wasn’t a glass Evian bottle, but it was a plastic one .This was much more elegant. The ring helped, too.

Tara said no, but thanked her 10 times as most Canadians do. The server left. We drank some water. And I urged Tara to hurry up because we had to leave to get to dinner. As she was getting ready and putting things in her purse as we sat on the hammock, I clicked record on the GoPro camera I had mounted because I was ‘shooting a video of our vacation’. I went to the champagne bucket and pulled out the ring which was now in a soaking wet box since I needed to unload it as soon as we got on the dock. Tight pants and a bulky ring box in the front left pocket isn’t obvious, or anything.

I circled back to the hammock and reminded Tara why the server asked if someone spilled their water.

Her face turned red. She remembered. I spilled her water the day I met her in the WFTV newsroom in Orlando. An awkward handshake. My arm bumped her bottle. Water spilled all over her scripts as she was heading into the booth to produce her show.

So I was essentially repaying my mistake. She bought it. She cried (a lot). Her mascara was everywhere. We sat and had a great time. Shot a champagne cork into the water and relaxed. But I assured her we were late to dinner. She demanded we go back to our house first. I said fine.


Dinner on the deck. A quiet, simple setup. A ridiculous meal to boot.

As we meandered through the dark forest of palm trees to our house, we came upon the lighted walkway of Tiki torches and three people standing in our house.

Those people are in the house! What the hell!?, Tara says with a shriek.

I said it was okay. We walked to the house. Tara met the chef and the server and manager. Dinner was served on the porch.

And to this day, I can honestly say that it was the best chicken I have ever had in my life. Along with way too much food we could barely eat.

The rest of the night was scrambling to find service to call our family and FaceTime all the details.

My plan had worked. No blimps. No arenas. No flash mobs. And certainly no on-air proposals.

Just a guy. A girl. A dock. And some damn good chicken.

The end.

The Proposal Weekend in Pictures