Trevor sets up Claire's friend Riley and a distrusting private investigator, as Claire walks the line between relationship expert and friend; Felix becomes smitten with the mother of Lita's new boyfriend.

Trevor helps a teenage boy set up his liberal mother, with his conservative boxing instructor, who happens to be his sperm-donor father; Claire's free-spirited mother comes to visit after another breakup with her boyfriend.

Trevor tries to unite an ex-con thief who is in love with his skeptical parole officer; after her apartment is robbed, Claire finds herself starting to rely on Trevor and crossing doctor-patient boundaries.

Trevor looks to set up an Iraq war veteran and his high school crush; Claire tries to come to grips with one of her fears, dancing in public.

Trying to match a radio deejay with one of his listeners, Trevor recruits indie-pop artist Robert Harrison to perform on their first date; Claire falls for a statistician helping her develop a test connecting potential mates based on commonalities.