At their weekly breakfast, Samantha tells the girls that she's back together with Richard. The girls are shocked and skeptical. Miranda is also shocked when Steve tells her he'd like baby Brady to be baptized so he doesn't go to Hell. Carrie relates that she's finding it difficult to drum up new material for her weekly sex column now that she's not in a relationship.

But just when she thinks she's going to get fired, Carrie finds out that a publisher is interested in turning her past columns into a book. She meets with the two single female publishers and is at a loss for words when they ask her to give her readers a message. Is she an optimist or a pessimist? Carrie wonders: Is hope a drug we need to go off of or is it keeping us alive?

Even Charlotte needs a little more hope and turns to a self-help program that touts the power of positive affirmations. She brings Carrie along to the next lecture and asks the speaker why her affirmations aren't working. The speaker tells Charlotte she needs to put her self out there, but Carrie stands up for her friend and says, "Believe me, she's out there."

Meanwhile, Miranda agrees to baptize Brady to make Steve (and his nutty mother) happy. She asks Carrie to be the godmother but Carrie worries that she's become too cynical to offer any guidance to Brady. Miranda will hear nothing of it - Carrie's her best friend. As the holy water is poured over Brady, Carrie hopes that it will wash away some of her "sin-icism." She goes home and decides to dedicate her book to Charlotte - the eternal optimist.

Carrie is appalled to see a mocked-up photo of herself all but naked on the proposed cover of her "Sex and the City" book. While browsing for book cover ideas at Barnes & Noble, Samantha offers to help Carrie create a look that says 'smart and sexy.' Charlotte heads for the Self Help aisle but when she sees the lonely desperate looking characters there, she flees. She refuses to identify with such women and opts to buy a book in the privacy of her own home - online.

Meanwhile in the privacy of Samantha's office, a hunky Worldwide Express guy delivers a 'package' that Samantha can't resist opening immediately. While Samantha provides a service of her own to the delivery guy, Carrie walks in and right back out. Back in her apartment, Carrie thinks about 'judgment.' She asks: "Should you judge a book by its cover?"

On a quest to slim down, Miranda, aka "Baby Fat," makes friends with a fellow Weight Watcher, Tom, aka "Big Boned." Post weigh-in session, they indulge in a taboo glazed donut together and then work off the calories in bed. Miranda enjoys Tom's moves until he kisses her with 'her' all over his face. On their second date, she gently alerts him to the problem but he can't handle the criticism and leaves saying he has to concentrate on his diet.

Things get tense between Carrie and Samantha as they disagree on the right look for the book cover. Carrie finds Samantha's selections a little too risque. Samantha accuses Carrie of judging her sexual behavior. A couple days later, Carrie apologizes for being judgmental. Sam relaxes and admits she judges herself too. With Samantha's help, Carrie wears a sexy short suit and holds her laptop for the cover shoot. She looks fabulous.