Real Wedding: Olivia and Damon Orobona

A Christmas present proposal led to this couple’s elegant St. Regis wedding.

When Damon Orobona met his studious University of Miami Law School peer Olivia Ley at a happy hour, he counted himself lucky to even see her outside the classroom. “Olivia was the most beautiful and sought-after girl in our law school class,” says Damon. “But she was also one of the best students, so it was difficult to get her away from the books long enough to talk to her.”

The couple’s first date was more of a study break—a quick lunch over sandwiches that turned into hours of talking. They’d been dating for eight years when Damon gave Olivia a special gift under the Christmas tree—a scrapbook that included the current date as the “date we got engaged”—right before he got down on one knee and proposed. A year and a half later, the couple wed in the St. Regis hotel courtyard on a gorgeous fall afternoon. An elegant reception followed indoors, where Olivia donned her mother’s traditional Chinese wedding dress for the cutting of their three-tiered cake. The couple danced to Eric Clapton’s “Wonderful Tonight” before a sparkler sendoff to their newly married life together.


Photographer: Andrea Jacobson, the Observatory

Venue/Caterer: St. Regis

Event Coordinator: Jessica Jennings, Something Blue Weddings

Florist: Amaryllis

Bride’s Gown: Custom design by Shin Bu

Groom’s Tux: Custom design by Indochino

Makeup: Mi Kung

Hair: Kristian Davis, Bella Bethesda Salon

Entertainment: Onyx

Transportation: Chariots for Hire

Associate Editor

Caroline Cunningham joined Washingtonian in 2014 after moving to the DC area from Cincinnati, where she interned and freelanced for Cincinnati Magazine and worked in content marketing. She currently resides in College Park.