Ashley met Jay when she went to Jamaica for her friend’s wedding. While out with her girlfriends the two met at a club. Ashley didn’t expect to talk to him again, but Jay tracked her down on social media. Six months later, Ashley went back to visit, and after spending just eight days together, Jay proposed. Ashley has had two failed engagements, so she’s hoping the third time is a charm, but with Jay being so young and having had a wild lifestyle, she’s hoping he can be serious about their relationship so that she’ll finally be able to stop searching for long lasting love.