James goes against Chloe's advice, succumbing to June's urging and attempting the unimaginable - dare we dream? -- a Dawson's Creek reunion! Along the way, he makes some shocking discoveries, veers slightly off course and encounters some stars of television past.

June receives her 1 year roommate evaluation from Chloe, in which she is shocked to find that she has been given a D. She eventually realizes that the only aspect in her life that she could possibly be slacking off in is her love life. Luther sets her up with James’ agent’s assistant, Will. Meanwhile, James is struggling to land an audition for a new Woody Allen film “Monte Carlo, Monte Carla.”

June discovers that Chloe has been attending Alcoholics Anonymous Meetings, to share her crazy partying stories as well as take free booze from the alcoholics. Pepper sets Mark up on a date with one of her friends, and June struggles to hide her jealousy. Meanwhile, James learns that he is on the short list for Woody Allen’s film “Monte Carlo, Monte Carla” but he may not get the role because Woody does not think he is deep enough.