Ava and Chloe discover -- for the first time -- that they both had a fling with the same guy. Unfortunately he's the fiancé of Emerson, their rich, new client who believes her man -- like her -- is a virgin. Meanwhile, Ava and her much younger husband go to a fertility specialist; thanks to a self-help book, Chloe realizes that no one has ever been "that into her," and Lola, who recently divorced after discovering her husband is gay, tries to re-enter the dating world.
To help cheer up a grief-stricken Lola as she gets over the death of her pet chicken, Ava invites her and the girls over to her apartment. They commiserate about what's missing in their lives and, after drowning their sorrows, are horrified the next morning to learn that each of them dialed someone on their cell phones while drunk. While Chloe thought she had called her eighth-grade boyfriend, she actually dialed the number of her highly-critical, overbearing mother (Christine Estabrook), who pays an unexpected visit.
Chloe, Lola and Emerson - who are all single - decide to look for love through a hot, new Internet dating service. Once online, Chloe becomes "Super Chloe" and is faced with choosing from among extreme sports enthusiasts responding; Lola poses as a gay man once she finds her gay ex-husband on the website; and Emerson dresses up as Audrey Hepburn to meet her perfect man, a surgeon who has invited her to breakfast at Tiffany's. Meanwhile, the already-married Ava decides to sign up just for fun, but her amusement turns to agony when the website makes her their featured profile.
Through mutual encouragement, the women decide it's time to take some risks that they wouldn't ordinarily take. When Ava's much-younger husband gets an acting job playing a teenager, she decides it's time to be honest with him about her real age. Chloe starts dating a man who is trying to fatten her up, but to her delight she finds it quite liberating. Meanwhile Lola begins therapy sessions with Sellers to find out why she's attracted to gay men, and Emerson must convince her wealthy parents to let her work at the real estate office.
When Charlie informs everyone that he has invested in a hot nightclub so that he can date super models, they analyze the notion of "dating up" or "dating down," and how the ideal situation lies balanced somewhere in-between. At the club, a young woman flirts with Ava's husband and she becomes concerned that his budding acting career may change the balanced dynamic in their marriage; Chloe and Emerson think they're "dating up," but are in for a surprise; Sellers tries to find balance by dating Danushka (Adrianne Curry), a gorgeous model with very low self-esteem; and Lola learns that "dating up" is not all about money.
To celebrate a big real estate sale, Ava surprises the ladies with a dream come true: four hard-to-get tickets to see Oprah Winfrey -- the woman they refer to as "kind of like our God" -- at a television taping in Chicago. Because it's their first time traveling together, problems arise and friendships and teamwork spirit get compromised. Matters turn worse when one of the priceless tickets goes missing and they're willing to do whatever it takes to get another one. But things start to look up when they have a chance encounter with Oprah's best friend, Gayle King. Back at the office, Sellers and Charlie, who don't understand why their officemates are so smitten with all things Oprah, learn firsthand about her effect on viewers.
A chapter in a book about relationships written by Charlie's ex-wife prompts Emerson to try and return her $50,000 engagement ring to her ex-fiance, Graham. But she can't bring herself to face him for fear of how she might feel. The others volunteer to return the ring -- but Graham's captivating and romantic ways to woo Emerson back prevents them from doing so. Meanwhile, in the spirit of returning things that don't belong to them, Ava decides to return her ex-boss' Rolodex to him, but when she tries to, he thinks she's trying to flirt with him.
When a sale falls through, the ladies find comfort in cleaning out their purses and, in the process, discover all sorts of things. Emerson finds the receipt for her never-worn wedding dress but, because of the store’s no-refund policy, is reluctant to ask for her money back. So Lola insists on accompanying her to the store to teach her some negotiating skills -- a must-have in the real estate business. Also, Ava finds a pile of receipts, bringing to light her shopping addiction, and Chloe recovers a phone number from a man she forgot she met -- so she decides to look him up.
To prove to the gorgeous Lola that people treat her special because of her looks and not just because she’s a nice person, Chloe challenges her to make herself plain and homely to see if people are indeed affected by her appearance. Meanwhile, Ava is convinced that the “fox factor” works, and is so displeased with her new driver’s license picture that she enlists Emerson, who went to photography camp as a youngster, to head to the DMV to take a better photograph.
Chloe, who lacks the holiday spirit, ends up in a cab accident while rushing to buy a last-minute gift for Ava’s toy giveaway. While in a state of limbo, Chloe is escorted on a journey by the three Ghosts of Christmas: Emerson, Lola and Ava -- from her past, present and future -- and they show her how her way of thinking will affect her and those she cares about.
When it appears that Lola’s sexy looks have caused a mysterious attack in her average-looking boyfriend, Fletcher, he is rushed to the hospital. For support, the ladies meet Lola there, and Chloe’s efforts to flirt with a cute doctor result in an unexpected medical procedure. Meanwhile Ava comforts a mother-to-be who asks her to be her birth coach.
Ava wonders if her happy marriage is in trouble and feels a little guilty when sparks fly between her and a client named Alec who, like her, has a much younger partner. Meanwhile Chloe, who wants a guy who’s more of a tiger than a pussycat, thinks her wish has come true when she meets a strong but silent bodyguard; Lola wonders if her new boyfriend will be able to look past their extremely different cultures; and Sellers has his own reasons for not wanting to set Emerson up with his friend.
Lola invites everyone over to her home to celebrate her country’s traditional holiday, El Día de Compasión – The Day of Forgiveness -- where they can forgive each other for the little slights and irritations made over the past year. But when their character flaws – such as being sarcastic, hot-tempered, nosey or chauvinistic -- are brought to light, they all strive to prove they’re not that way.