An obstacle arises in Jack and Scruffy's relationship, and Oona runs into Drew and his new lover.

Oona is unhappy with Russell. Jack and Mitchell take another step in repairing their friendship as Mitchell and Oona have a fight.

Flashback to the destruction of Jack and Mitchell's relationship.

Jack agrees to pick up a horribly drunk Mitchell from Oona's apartment.

Jack has a moment with Julia Roberts, Oona branches out professionally, and Mitchell turns on the charm.

Jack gets more than he bargained for when he tries to pick up a stranger in Williamsburg, and Oona decides that revenge is a dish best served in a little black dress.

Following their ugly breakup, Mitchell and Jack navigate gay life in New York.