Jack challenges Elliott to a game of darts and hits him in the back when Elliott accuses him of being too competitive. Meanwhile, Nina reveals that she had a daughter 34 years ago that she gave up for adoption, and her daughter is trying to find her. Nina enlists Finch to pose as her ""son"" but when she tells her daughter the truth, she wants nothing to do with her. Trying to make amends, Nina discovers that she is a grandmother also.

Nina is trying so spend some quality time with her granddaughter Tess. Chloe asks Nina to keep Tess from bars, boys and clubs, but all Tess wants is to get wild. She throws herself at men at a bar and later at Finch, who pretends to be the magazine's editor. When Tess runs away, Chloe and Nina find her at Dennis's, and they all offer to sleep with him in order to keep Tess from doing so. Meanwhile, Jack insists on giving Maya a birthday present, but has no luck with his ideas or Elliot's. She gets mad not because of the meaningless gifts, but because it's really not her birthday and her father should know better. Still, they both feel like it's someone's birthday – and it is: Maya's mother!

Finch forgets to tell Jack about an important meeting with foreign clients, so he assumes Jack's identity and attempts to close a deal without Jack's knowledge. Meanwhile, Nina and her rock star boyfriend Simon (guest star Simon Templeman) force themselves to go clean in an attempt to get Nina's hard-partying granddaughter (guest star Sasha Barrese) to change her ways, and Elliott seizes an opportunity to confront his high school bully (guest star Jason Marsden).