Dylan, a 20-something romantic, has been intimate with a long list of women during his quest for true love. When he discovers that he has a sexually transmitted disease, Dylan must go back and contact everyone he has slept with to tell them about his diagnosis. Each time Dylan seeks out a different person from his contact list, the show flashes back to a defining moment in a relationship that he would prefer to forget. Friends Evie and Luke, who have been with Dylan through it all over the last decade, travel down memory lane with him.