An old college friend rings up Fiona with a peculiar problem, while a phone call from Conan O'Brien comes with some unsolicited advice.

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.