Jessie & Gregory

Jessie Packer Kaplan & Gregory Lamont Alston, Jr. on July 14, 2018

By Thor Christensen / Published in the July 2019 issue of Newport Life magazine

Jessie and Greg first met each other in October 2011. Before online dating became as popular as it is now, they found each other on the Plenty of Fish app. After chatting for a few weeks, they decided to get together for the first time. Conveniently for them, Halloween was just around the corner. They met up at a Halloween party in Greg’s hometown of Washington, D.C., and clicked very quickly from there. The couple dated for almost five years before getting engaged in 2016, and got married in 2018 — almost exactly two years from their engagement date. 

“We both wrote our own vows, and there wasn’t a dry eye between us and our guests.”

It’s Him

Jessie and Greg’s personalities complement each other brilliantly. Their wonderful senses of humor, coupled with knowing exactly what the other has in mind, provide a perfect unity of emotion and passion. Jessie also suffers from Type 1 diabetes, and Greg’s unwavering support convinced Jessie that Greg truly was the one.

Shipping Up to … Newport?

Newport has been a part of Jessie and Greg’s lives for a long time. Jessie’s grandmother grew up in Newport, and her great-grandfather owned a shoe store in downtown Newport for more than 60 years, in the location that is now Brick Alley Pub, which happens to display his photos and story. Jessie spent the summers visiting her family and working in Middletown. The island has become a haven of memories for Jessie and Greg, including the proposal.

Cementing Their Unity

In July 2016, Greg proposed to Jessie in front of her family’s summer home in Middletown, overlooking Easton’s Beach. He was extremely nervous, stuffing his face all day just to calm himself down. Greg’s proposal was also witnessed by his mother, who came all the way from Washington, D.C., for the occasion. Their wedding produced multiple cherished, memorable moments, including their first dance to “You Are” by Charlie Wilson, and the reading of the vows they wrote for each other.

Where Are They Now?

After honeymooning at Secrets Playa Mujeres in Mexico, Jessie and Greg moved down to Silver Spring, Maryland, near Greg’s hometown, in order to be closer to his family. Jessie’s parents currently reside in Newton, Massachusetts. Jessie works as an executive assistant to the principal at a local high school, while Greg works as a paralegal for Fragomen.

Featured Vendors

Photographer: Victoria Comfort Photography
Bridesmaids’ Dresses: Azazie
Tuxedos/Suits: Indochino
Rings/Bands: Mervis Diamonds
Invitations: Minted
Rehearsal Dinner: Newport Beach House
Venue & Caterer: The Atlantic Resort at Wyndham Newport Hotel
Hair & Makeup: Allison Barbera Beauty
Nails: Charming Nails
Flowers: Golden Gate Studios
Cake: Scrumptions
Transportation: Valet Park of America
Ceremony Music & Reception entertainment: Music Machine Entertainment
Videographer: 1st Row Films
Planner: Sweet Deets Events
Wedding Night Stay: Wyndham Newport Hotel
Guest Accommodations: Wyndham Newport Hotel
Linen/Décor Rental: XO the Girls
Brunch: Newport Tent Company, Tom’s Market Catering