Will's got a new girlfriend, Dani, who insists on having Claude run errands for her. Ramona and Owen convince Claude to put her feet down and stop being a pushover for Dani. When she finally confronts Will's new girlfriend, she imposes him to choose between her and Claude. Although happy to see Dani out of her life, Claude has to put aside the pride and talk her into getting back together with Will, who's been miserable without her. Meanwhile, Lydia and Kipp start sucking up to Ramona and Owen when they find out they have access to the VIP area at an important party.

After breaking up with Charlie, Claude is feeling low. Will's fiance insists Claude accompany her to a bridal salon, which only serves to upset Claude further. They run into Trista Rehn (star of ABC's reality show, The Bachelorette), who got engaged on the show and is trying on wedding gowns. Claude locks herself in a dressing room to cry, wiping her nose on a wedding gown, and Trista trys to comfort her through the door. Claude's friends rally round, even Lidia, and try to cheer Claude with an impromptu slumber party and girl talk.

Claude takes on the task of personally shopping for all of Will's Christmas presents for staff and later for his girlfriend, Dani. Her efforts start to go awry when Lydia and Dani's gifts get switched, making Jeb jealous and offending Dani.