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Fed up with her lack of a love life, Alex (Amanda Peet) devises a way to take her relationship with her boyfriend Ben (guest star Matt Letscher) to the next level. Meanwhile, in spite of his feelings for Alex, Pete (David Walton) rekindles his romance with ex-girlfriend Natalie (guest star Diora Baird), but repercussions quickly unfold. Elsewhere, with hopes of winning over Alex, Pete and Ben vie for Charlie's (Joey King) attention.