Sharp had Napravnik ride a horse for him at Penn National in 2009, and they began dating a few months later, becoming engaged in 2011. Sharp, a horse trainer, was born in Martinsburg, West Virginia. He is an only child and grew up around horses. His father, Marc Sharp, is a trainer who also owns a horse farm near Harpers Ferry, West Virginia. His mother, Sara Escudero, was an exercise rider. The pair divorced and Sharp split his time between them, growing up in Kentucky and West Virginia. Sharp was a jockey from 2004 to 2005, riding mostly at Canterbury Park in Minnesota, but also in West Virginia and Maryland. Sharp was an assistant trainer to Mike Stidham for four years, and then for three years an assistant to Mike Maker, where he ran Maker's operations in New York, Kentucky and New Orleans. Napravnik and Sharp sometimes competed against each other when a horse Sharp trained was running against one Napravnik was riding, but the two were a trainer-rider team for Ramsey's three-year-old colt, Vicar's In Trouble, who won the Louisiana Derby and contested the 2014 Kentucky Derby. In August 2014, Sharp left Maker's barn to begin an independent horse training stable, with the full support of both Maker and Napravnik. He scored his first graded stakes win on May 16, 2015 on the Preakness undercard with the Ramsey's horse Sandbar in the Grade III Maryland Sprint Handicap. In 2017, Sharp won the Louisiana Derby with Girvin, a colt who was Sharp's first starter in the 2017 Kentucky Derby. Napravnik was the exercise rider for the colt at Sharp's training stable, and commented, "I thought about putting out something on Twitter . . . saying I was going to ride Girvin, as an April Fool’s joke, but I was worried people might take it seriously." Of the couple's relationship, Sharp has stated, "Some guys might think being married to someone as famous as Rosie is a tough position, but I don't, I'm very proud of her." Sharp and Napravnik split their time between homes in Louisville and New Orleans. Besides working with horses, the pair also provide foster care to rescue dogs. Napravnik obtained her jockey license in 2005 at Pimlico Race Course. She won her first race as a licensed jockey on June 9 of that year, riding Small's horse, Ringofdiamonds. She initially rode under the name "A.R. Napravnik" to conceal her gender.