Chris pressures John into setting a time and place for their first date. Hector convinces Jake to make extra money by sampling experimental medications. Linda makes Margaret feel guilty for talking her way out of a traffic ticket.
Becker tries to plan a romantic first date with Chris, but unforeseen obstacles constantly appear. Jake receives shocking news about his grandmother after she dies in a retirement home.
Chris is frustrated when John repeatedly refuses to maintain his side of a conversation. Linda claims that she has met "the one." Hector tries to persuade Jake to invest in his latest get-rich-quick scheme.
Chris tries to get John to be more considerate of her feelings. Margaret takes a night job with a telemarketer. Hector tricks Jake into selling porn magazines.
Chris is incensed when Becker receives a free trip to Las Vegas and doesn't invite her. An "odd duck" plastic surgeon takes over Becker's practice during his absence.
Margaret is depressed about her career path after hearing about a childhood friend who has become wealthy. Becker tries to train Linda to give flu shots.
Chris plans a trip to Bermuda with Becker. Margaret looks forward to a weekend without Louis. A psychic tells Linda she's going to meet the man of her dreams.
Linda deletes some important files and spends the day trying to recover them or cover up what she's done. Some out-of-town friends have come to see John but he's nowhere to be seen so Chris must entertain them, to the annoyance and embarrassment of all concerned. John is trying to get home on the subway but a little old lady needs help in getting to her destination. John stops to help her, but she needs to be helped again and again. And when he finally gets her to the station she's heading for, Chambers Street, why doesn't she want to go up to the street?
Chris fears that John is going to break up with her after he invites her to dinner at a nice restaurant with no explanation. Jake decides how to spend his inheritance from his grandmother. Linda finds a boyfriend.