From the first meal they ever shared together, Ashley Gallardo knew Samantha Silveira was undeniably the one. “We initially met on a dating app and finally mustered up the courage to meet in person for a dinner date,” said Ashley. Four years and many meals later, Ashley wanted to make things official.

“I planned to propose to Sam on Martha’s Vineyard as it is one of my favorite places,” she said. “The Island holds some of my most cherished memories.”

To get the proposal ball rolling, Ashley searched the internet and found Island photographer Mila Lowe to help capture the moment. “I adored her intimate, natural style,” she said.

Ashley chose to pop the question at the Gay Head Cliffs in Aquinnah prior to a dinner at the adjacent Outermost Inn. To get Sam down to the beach where Lowe was waiting, Ashley suggested they take a walk.

But Sam is the kind of woman who does not miss a beat, and in the minutes leading up to the proposal, she became suspicious that this may be the big day. It was very hot, Ashley said, and right before they started walking down to the cliffs, Sam asked her why she was wearing a jean jacket. “I was adamant about keeping it on. I needed to keep the ring hidden and secure.”

Once on the beach, things went off without a hitch: Sam said yes, and Lowe photographed it exactly how Ashley had dreamed.

A beach wedding in Aruba is set for June 2025.