The couple didn't have the easiest season, starting off in a long distance relationship before being pushed together when Checketts unexpectedly joined White's charter as a chef. The Daily Dish notes White was slightly peeved that her boyfriend's arrival took some of the shine off her becoming bosun. She was also concerned about mixing business and pleasure, particularly given her previous bad experience during season two.

White fretted at the time, "My fear is how it could affect our relationship because I love Below Deck, but it's not worth my relationship — not with him, not with this one." It seems work was what ultimately drove them apart, as White explained to Cohen, "This industry is tough. We work apart for a long time." However, she also ominously noted, "There's some bad apples out there," suggesting that something more damaging might have occurred, too.