Because the pair loves Christmas, they’re hoping for a December 2027 wedding.
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David Young proposed to Olivia Jo Wilson at the W Philadelphia. / Photography by Angela Gaspar Photography
What’s more romantic than a view of the Philly skyline? How about a proposal overlooking the city? That’s why the W Philadelphia’s terrace remains a popular spot for popping the question, with everyone from Eagles wide receiver DeVonta Smith to pro golfer Matthew Wolff getting down on one knee there. Here, you’ll read about another big moment, staged shortly before the holidays and captured by Angela Gaspar Photography. Need even more proposal inspo? Click here.
The couple: Olivia Jo Wilson, 24, and David Young, 24, both of Elkton, Maryland
How they met: David and Olivia have known each other most of their lives. They attended elementary school, middle school, and high school together; but didn’t start dating until December 2019, when they took a trip to New York City.
The proposal: David and Olivia both love Christmas — so what better way to kick off the holiday season than with a November proposal? The engagement, which took place at the W Philadelphia, was a family affair. David’s mother decorated the terrace — which boasts stunning views of the city skyline — with candles, lanterns, rose petals, and four white rose, hydrangea, and lily floral arrangements, which she made herself. Olivia’s mother and Olivia’s best friend also helped out. And they all made sure David and Olivia’s one-year-old son was there for the big moment. After the “yes”? Champagne was popped, and the couple’s family and friends joined them on the terrace to celebrate.
Her reaction: Olivia says she was in utter shock. “I just felt so much love in the moment,” she says. “It was beautiful in every way, and it was so special.”
His reaction: Dave simply wanted everything to go off without a hitch. “I wanted to make it special for her because she is so special to me,” he says.
The post-proposal moments: The couple later enjoyed dinner at Butcher and Singer, where Dave revealed he had one more surprise: He’d invited their friends to celebrate their engagement with a night out in the city. “We walked all around town and enjoyed the night life,” Olivia says of the after-dinner festivities.
The wedding plans: Dave and Olivia are soaking up that soon-to-be-wed feeling right now — and since they both love Christmas, they’re eyeing a December 2027 wedding.
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