When Jill's co-worker Stan takes credit for his idea, Jill challenges him to a boxing match at Mikey's Office Fight Night at the bar. Jack and Matt cover the story of Jill's fight for WNKW and which causes Jill's jealousy to rise. Meanwhile, Barto asks Audrey out to celebrate a good review of her musical and Elisa feels a connection with a stranger she passes on the street.

Jill's suspicions are aroused when he sees Matt with another women, and he contemplates telling Jack. Meanwhile, Jill's tactless girlfriend offends Mikey.

Jack pitches an idea to her new boss for a newscast segment that she would produce and appear in; Jill and Mikey try out a karaoke machine for the bar. Elsewhere, Barto is jealous of Sarah's crowded social schedule, so he decides to pursue other women; Audrey interviews potential roommates and meets a guy who may perfect for her.