Strangers With Candy: Bogie Nights (1999)

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Jerri (Amy Sedaris) and Orlando's (Orlando Pabotoy) friendship is put to the test when a new student arrives at Flatpoint High in this episode of the edgy Comedy Central series. Instantly attracted to new arrival Ricky despite the fact that everyone seems out to get him, Jerri quickly caves to peer pressure and humiliates Ricky at every possible opportunity. When Orlando presents Jerri with a friendship collage, Jerri promptly modifies it and presents it to Ricky in hopes that he will join her at the golf-themed Bogie Nights dance despite Principal Blackman's objections. After a jealous Orlando tips off Mr. Jellineck (Paul Dinello) as to how much time Jerri has been spending with the new guy, Jerri's jealous friend attempts to cause trouble for Ricky at every turn. Confronted by the girls in her class as to the nature of her relationship with Ricky, Jerri reluctantly informs them that she will be attending the dance with sociopathic Spike. When Ricky appears at the dance to inform Jerri that he will soon be leaving Flatpoint, Orlando urges the students to beat Ricky with their golf clubs, resulting in an impassioned plea for tolerance from Jerri. Touched at Jerri's dedication to Ricky, Principal Blackman (Greg Hollimon) declares the couple "Mistress and Master of Bogie Nights" before Spike returns from the bathroom and attempts to attack Ricky. After saving Ricky by crashing her golf cart into Spike, Jerri and Ricky head to the parking lot to make out -- only to discover that Ricky is in fact Jerri's long-lost son. ~ Jason Buchanan, Rovi