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Ashlee & James

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James White

and

Ashlee Shepard

April 19, 2024

Montego Bay, St. James Parish

How They Met

Down in the DM

Ironically, Ashlee and James grew up going to school together from 8th grade until senior year in high school. They even had English class together senior year. James sat in the desk behind Ashlee, but they didn’t speak much. It wasn’t until college when they began to converse. James initiated the conversion by sliding in Ashlee’s direct messages (DM) on Instagram. The instant connection was felt by both. After a few months of hanging out, James knew he couldn’t let Ashlee get away. On September 13, 2016, Ashlee and James became girlfriend and boyfriend.

The First Date

Baby, You’re a Firework

Ashlee and James’ “first date” was on the 4th of July at her dad’s house for her sister’s pool party. They sat in the pool under the fireworks and got to know one another. Just like the fireworks, they had a spark! Their “official first date” was shortly after the 4th of July at a bowling alley. As many of you may know, James is a true competitor through and through. Even on their first date, he wouldn’t let Ashlee win. They shared many laughs, many stories, and many drinks. The only thing Ashlee won that night was his heart.

The Proposal

Put a Ring on It

James proposed to Ashlee September 2022. Ashlee and James were supposed to be going to dinner to celebrate their dating anniversary at Brenner’s on the Bayou. The steak house is surrounded by the wonder of nature with lush foliage and a cascading waterfall. James asked Ashlee if she would like to take a stroll around the property while they waited for their table. James lead Ashlee to this beautiful gazebo with an amazing view. As Ashlee was taking in the scenery, James got on one knee and asked, “Will You Marry Me?”. With no hesitation, Ashlee answered, “Yes”!

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