Ally McBeal

S05E08 Playing With Matches

With Jenny's mom's wedding on the horizon, Ally is taken aback when Tim gives her a suggestive glance. Curious, she confides in Jenny, and they devise a plan to test his intentions. When Ally makes a flirtatious advance, Tim surprisingly proposes they have an affair. To Ally's astonishment, Jenny's mom is accepting of this, adding to Ally's confusion. She begins experiencing visions of a 7-year-old boy, who represents her younger self when she still believed in love—a realization brought to light by Richard, rooted in the pain of losing Billy and Larry. Meanwhile, John and Coretta assist Kimmie Bishop, who has returned to sue a matchmaker for labeling her "unmatchable."