Annie thinks the black pearls she found in a taxi are fake but really belonged to Elizabeth Taylor.
When Roger's father, Nick shows up unexpectedly, Annie tries to convince Roger that his dad probably wants to make up for lost time, but Roger can't help being suspicious of the father he has barely known. While Roger's dad is in town, Elliot moves in with Didi, but Didi immediately regrets inviting him after she excitedly appoints him her ""diet cop"" and he takes the job a little too seriously.
When Didi lands a job assisting a famous playwright, Annie lands a date with a handsome actor and Elliot convinces Didi to show her new boss his play. Meanwhile, Roger considers mending his womanizing ways when he falls for an independent career woman who asks him out and then dumps him after only one date.
Annie gets cold feet after she sees the webbed ones belonging to a doctor she's dating; and later finds that she wasn't the only one concerned about appearances. Meanwhile, Elliot has dreams about murdering Roger.
When Didi realizes that her irresponsible boy-friend isn't going to show up for her birthday, Annie O'Donnell uses a $100 off coupon and a virgin visa card with a $400 limit that she was saving for her honeymoon to treat Didi to a glamorous night at the Plaza Hotel. While the two girls attempt to live like queens on a serf budget, Roger and Elliot do some male bonding and discover that when it comes to women, they don't have anything in common.