When Claude is unexpectedly asked out for dinner with Will, she quickly cancels her double-date plan with Ramona. But when the ""date"" turns out to be less of one than she anticipated, Claude finds solace in the company of Lydia -- who assumes that Claude slept with him. Meanwhile, Owen tries to assert authority over Kipp and the two feud over an expensive pen.

Claude scores a date with Charlie from travel after accidentally throwing her hair on his face. They have a wonderful time together, and the next morning Claude is ecstatic about it. Will introduces her his godson Oliver, and asks Claude to show him around town. He asks her out on a date, and ends up accepting to go out with him after Will pressures her to. Claude tries to jiggle dating two men, but her scheme soon falls apart when Will comments on her date with Oliver in front of Charlie, who leaves heartbroken. Claude feels bad gets advice from Ramona and Lydia on how to dump Oliver and get back with Charlie. Meanwhile, Kipp starts sucking up to Mr. Turnbach's son hoping for a chance of a promotion.

Claude is throwing her first Thanksgiving for all her friends. Owen's two lesbian moms (Valerie Harper and Joanna Kerns) come to visit and share the holiday. The only problem is that his moms have always assumed that Owen is gay. Hoping to keep up the ruse, Owen asks his friends to play along, including asking Carl to pose as his lover. Meanwhile, Lydia and Kipp both get invited to Will's Thanksgiving party, where Kipp is briefly the star attraction.

Claude nudges Jeb into marrying Lydia, so she'll stay home and be out of her hair for good. Meanwhile, Jeb instructs Kipp to recruit guests for a post-proposal ""man party.""

On the day after Thanksgiving, Owen's two mothers pay a visit to the staff at GNB and begin meddling in their lives. Judy (Joanna Kerns) advises Will on his issues with women, while Judith (Valerie Harper) lives vicariously through Carl and Ramona, encouraging them to indulge in her passions for gambling and drinking. Meanwhile, Claude fears that she'll lose her job when Owen blabs about her interview for another job; and Lydia fears that she'll lose Jeb because she accidentally killed his ""Gamma Toots"" at his family's Thanksgiving celebration.