PodcastsJan 12, 2026
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IndependentsAug 19, 2020
This Sky-High Proposal Will Warm Your Heart
J.R. Dunn Jewelers’ “Say it Big” proposal giveaway let one lucky man pop the question in an unforgettable way.
Patrick Callahan proposed to his fiancée Taylor via this billboard overlooking Florida’s I-95. (Photo courtesy of Christina Cernik Photography)
Lighthouse Point, Fl.—Patrick Callahan was not content to just get down on one knee and pop the question to his now-fiancée Taylor.
Callahan won in March, but COVID-19 restrictions put his proposal plans on hold for a while.
After a few reschedulings, he found the perfect time in early August when he took Taylor, his girlfriend of six years, for a birthday trip down to the Florida Keys.
They made a pit stop in Miami at the Deering Estate, a stately oceanside 1920’s manor, once home to businessman Charles Deering.
Standing between two rows of palm trees, he presented Taylor with a solitaire round diamond engagement ring from J.R. Dunn Jewelers.
The couple then drove to a surprise dinner with their family and friends.
On the way, Callahan pulled over to show Taylor her next surprise—a huge billboard that read “Taylor, will you marry me? -Patrick”, complete with one of her favorite photos of them together.
Callahan arranged for a lift to bring the couples up closer to the billboard for a photo shoot (see below).
The two finally made it to the Keys to celebrate.
“A huge congratulations to the future Mr. and Mrs. Callahan and cheers to many more special moments like this epic South Florida proposal,” said J.R. Dunn in a press release about the proposal.
Founded in 1969, J.R. Dunn Jewelers is a second-generation, family-owned jeweler based in South Florida.
WATCH: Patrick and Taylor’s Proposal Video
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