Chloe takes it upon herself to teach June to be sexually empowered and to dabble in some casual encounters. However Chloe's own sex life catches up to her, and to James, when their old sex tape leaks out to the public and James freaks out on how this will affect his likeability.
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This series was intentionally aired out of the producers' intended order, which was for two seasons of 13 episodes each.
Per James van der Beek, the intended airing order for this episode is season 1, episode 8.