Julia tries to cheer up Caroline by setting her up on a blind date, which Richard does his best to sabotage. Meanwhile, Annie prepares to realize her dreams of revenge at her high-school reunion, with an overly coached Del in tow pretending to be her highly successful husband.

While they wait for Chinese takeaway delivery, Richard shows Caroline a family wedding ring he was planning to give to Julia, and soon after, the heirloom seemingly disappears from her apartment -leading Fong to accuse, and throw out, his delivery boy son Tim, who takes up residence in Caroline's living room. Meanwhile, Del and Charlie scheme to climb to the top of the Rockefeller Center Christmas tree to place a large ad for Caroline's line of holiday cards; and Annie develops a cabaret act and is attracted to hunky guitarist Paul, while oblivious to pianist Seth's growing infatuation with her.