A Modest (Cockenoe) Proposal

Megan Huntley — a Westport native — graduated from Staples in 2007. Tyler Kupper is a 2003 Weston High grad, who played hockey on the Wreckers’ co-op team.

They did not know each other — even though they spent many summers, boating on Cockenoe Island.

Tyler owned a thriving Christmas tree business in New York City. The last tree he delivered before selling his company was to Megan.

It was his best delivery ever. They started dating. And even though they both now live in the city, they spent as many weekends as they could here, on the water.

So when Tyler decided to propose, Cockenoe was the perfect choice.

Cockenoe Island, off Compo Beach — a favorite destination for local boaters.

He contacted Westporter Dave Dellinger, to (secretly) photograph the event. The two had been colleagues at the United States Tennis Association.

Together, they planned the day: Saturday, August 18.

It was stressful for Tyler, as it is for any guy about to pop the question. But Dave worried too: There was a 95% chance of thunderstorms.

Dave made his way out to Cockenoe, on his brother’s boat and a kayak. Then he waited for the couple.

He photographed their arrival …

… a few tender words …

… and the proposal.

(Photos/Dave Dellinger)

Megan was completely surprised.  (Fortunately, she said yes.)

Best of all, the rain held off — and the sky was blue.

It was just another day on Cockenoe for the egrets and other wildlife.

But for Tyler, Megan — and Dave — it was one they’ll never forget.

6 responses to “A Modest (Cockenoe) Proposal

  1. Beautiful story!

  2. Betsy Phillips-Kahn

    What a Romantic Story!!! Congratulations to you both– ❤️

  3. Such a sweet story! Congratulations to you both. Knew Tyler as a boy through his mom. Always so nice, kind and hardworking. I love hearing stories like these to start your day.

  4. Adorable Westport story. We were fortunate to know Megan growing up. She is a smart, beautiful, talented young lady. And Tyler is obviously a very cool guy as evidenced by his proposal. Wishing you many years of happiness!

  5. What a beautiful story!

  6. Lovely. And nicely photographed too!

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