Advice guru Fiona Wallace develops a new brand of three-minute therapy for the Internet and takes on a client whose unique problem could help her promote her services.

Frustrated by her marriage, Fiona flirts with several men, while plotting to exploit the sexual issues of a client in order to impress a potential investor.

Fiona's old friend Newell tries to spark a romance with her; and she and Conan O'Brien square off against each other. Meanwhile, Fiona's mother looks to have lost her grip on reality again.

Newell is still bent out of shape over an experience he and Fiona shared in college 20 years ago; and Putsy gets caught up in a legal entanglement. Later, a disappointed Fiona learns that an old flame may finally be over her.

Fiona cures Newell of his obsession, but her handling of Robin has disastrous consequences for Kip's campaign; Fiona is surprised to find that Austen isn't flying solo anymore.