Jack + Carly’s Ocean Ave Proposal in Newport, RI
So here’s how it started: I was driving to a meeting when Jack called me out of the blue. Honestly, I love a good spontaneous call—especially when it’s about planning a surprise proposal. They are one of my favorites!
Carly had visited Newport years ago with her girlfriends and totally fell in love with the place. So Jack, being the thoughtful guy he is, decided to plan a weekend getaway and pop the question somewhere she already held close to her heart. Romantic and strategic? We love to see it.
Problem was—Jack had never been to Newport. So we put our heads together on the phone and figured out everything: the perfect proposal spot, a solid timeline, and exactly how to get them there without tipping Carly off.
The weather? Windy, but surprisingly not too cold for an early summer evening (a rare Newport win).
As for Carly? She had zero clue. Jack told her they were headed to Castle Hill for a drink on the lawn—something she remembered loving from her last trip. Smooth, right?
When they got near Ocean Ave, Jack casually suggested they stop to take a “quick selfie with the ocean.” Classic move. She went along with it... and then boom—proposal time. Cue the happy tears, laughter, hugs, and one very big YES.
After soaking in the moment (and snapping all the magic), we hit a few more dreamy spots: Hazard Road to escape the wind a bit, and the Newport Golf Club entrance because… that backdrop? Unreal.
Carly was absolutely glowing—calling friends, hugging Jack, just radiating that newly-engaged energy. The whole vibe was so joyful and effortless. These two nailed it.
Huge thanks to Jack for the call—and the trust to help make it all happen.
Now go check out the photos. You’ll feel the love.
