Susan is appalled when she misses a deadline but discovers that Nana covered for her by submitting an article in her stead - which Jack and her fans think is the best thing she's ever written. Desperate to find an idea for an even better column, Susan ultimately does the obvious: writes a confession about the previous column. Meanwhile, there's a big change in Vicky's life when she finds a wallet and falls for its handsome owner, only to discover that he's a rabbi.
A background check is in order when Susan agrees to meet a gentleman who sent her a rare book as a token of his readership appreciation - and who turns out to be still in high school. Meanwhile, Jack plays pimp for his ugly pooch; and stress takes its toll on Todd when he is put in charge of the magazine's new web site.
Family conflict rises to the top of the agenda at the funeral of Susan's grandfather, since Liz wants a traditional funeral while Nana wants a party to celebrate her spouse's wonderful life, and Susan is too busy organizing a tribute to her grandfather to deal with her own grief. Meanwhile Vicky, Todd and Luis go to the wrong funeral home and find themselves comforting the wrong widow; and Jack becomes the reluctant owner of a very, very ugly dog.
Margo's drunk with power during her divorce proceedings with Jack, thanks to Susan's inadvertent slip about Jack's intoxicating past: she interprets the fact that Jack fell asleep on Susan's couch as evidence that he had an affair with her, thus violating their pre-nuptial agreement. Now Susan must testify in court about her true feelings for Jack. Meanwhile, Vicky becomes obsessed with the idea that someone is tampering with her lunch; and Todd begs Luis to teach him how to dance.
Deciding to go after the new investigative reporter position Jack has created, Susan reluctantly seeks professional advice from her old high school rival Maddy Piper, now an established and aggressive journalist - who quickly infiltrates Susan's professional and personal lives by double-crossing her, getting the story and the job, and displaying considerable interest in Jack. Meanwhile, Vicky is being driven crazy by the fact that the bagel delivery guy shows no sign of remembering the night they spent together; and Todd is disturbed by the fact that his web-surfing inevitably lands him in lesbian chat rooms.
While Susan prepares to fly to Venice with Cooper, Jack tries to find the courage to utter three, make that five, little words about his feelings for her. He fails -- but Susan, having figured it out, has a miserable time with Cooper in Europe. After rejecting Cooper's extremely premature marriage proposal and returning home, she confronts Jack, accusing him of using her to compete with Cooper. Jack finally convinces her that his feelings are genuine -- but Susan tells him that she doesn't love him.