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When Chelsea goes out of town, Charlie spends the day trying to help a depressed Jake win back Celeste. Jake wrote a song for her that he planned on playing for her, but Charlie convinces him to go for a more honest approach. Unfortunately, that doesn't work for Jake, but at the end of the episode a new girl calls to meet him at the pier. Score one for the uggo.
Meanwhile, Alan is desperate for human contact and when Charlie refuses to hang out with him, asks Herb (Ryan Stiles) on a man date after he drops off Jake. The two of them go to the mall for kebabs, but when Judith calls, Herb heads running back. The next day, Alan goes to pick up Herb for their date at the flea market and Judith tries to nip the relationship in the bud. Alan goes around back and throws stones at Herb's window and he attempts to sneak down a lattice and falls, injuring his neck. At the end of the episode, Herbs sneaks over while he's supposed to be at the physical therapist to spend time with Alan.