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 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.