This episode is an adaption of "The Batman Adventures: Mad Love", the critically acclaimed single-issue comic from the Batman: The Animated Series (1992) spin-off comic series set in the animated continuity. The story was written by Paul Dini and Bruce Timm, two creators from the show, and tells the origin story of the Joker's henchwoman Harley Quinn. It presents her past as a psychologist at Arkham Asylum who then falls in love with The Joker. This story won the Eisner Award for "Best Single Story" and the Harvey Award for "Best Single Issue or Story" in 1994. Harley Quinn's origin was only hinted at in a few episodes of Batman: The Animated Series (1992), both aired in 1994, in Trial (1994) it's mentioned that Harley was once a psychologist once at Arkham and that's when she'd met the Joker and in Harlequinade (1994) Batman in genuine confusion asked Harley about her sick attraction to the Joker.
Before being adapted as an episode of this series, "The Batman Adventures: Mad Love" story was pitched as a straight-to-video film. There was a lot of fans wanting the comic to be adapted as an animated series episode or direct to movie according to writer Paul Dini, and he and Bruce Timm were looking into it into a home video movie adaptation after production on the animated series ceased. However, Dini said that was unlikely to happen in a September 1995 interview saying, "it's a story we could never tell on the show. It's a little too sexy and a little too violent for the series." However, when this series was green-lit for Kids WB, the creative team were able to adapt the story for a 22-minute episode near verbatim to the comic with only a few minor changes.
The Joker says, "May the floss be with you," an obvious nod to the Star Wars: Episode IV - A New Hope (1977) line, "May the Force be with you." The Joker is voiced by Mark Hamill, who played Luke Skywalker in the "Star Wars" films. The original line from the comic was "watch those in between meal snacks".
When Comissioner Gordon walks into the dental office, the name on the door is "Dr. J. Reko", an anagram of "Joker". In, the comic, the fake name on the dental office door was "Dr. Laffo".
At one point Harley asks the Joker, "Don't you wanna rev up your Harley?" This is a reference to the iconic brand of Harley-Davidson motorcycles, which are often referred to as Harleys.