When Chelsea gets a D.U.I., she realizes she needs to make some big changes in her life, including moving closer to where she works - Jerry's Ultimate Sports Bar. She and her best pal Olivia, discover an apartment in the same building as their colleague Rick - just blocks from the bar - and move in immediately with the quirky and good-natured Dee Dee. Meanwhile, Sloane, whose military husband is currently stationed overseas, is due to give birth any day and is not convinced she can count on the freewheeling Chelsea to be there for her at the delivery.
When Sloane's old high school boyfriend Matt Gunn, shows up at the bar, Chelsea's adolescent fantasies are awakened and despite Sloane's objections, Chelsea can't resist the temptation to go out with him. Meanwhile, Rick tracks down his old girlfriend Nikki to reconnect and finds out she's now engaged to someone else.
Angelic teenage pop singer-guitarist Luke is the star at a church chastity party for bachelors, becoming desired by every girl. Chelsea gets him 'intamately', but hearing he's still a virgin before the go all the way decides against him altogether. Realizing Lukee would be perfect for her couch-addicted virgin flatmate Dee Dee, she matches them, but precisely their kisses turn her off, until Rick suggest TV-style romance.
However much waitress Nikki Natoli is loathed, her fiancé proves a welcome gentleman, presented to her grandmother, whom Cheslea grudgingly puts up, just like the stray dog Dee Dee took in. At the wedding, things go wrong as the charming groom comes to his senses and bails on Niki.
When Chelsea learns that their customer Tim Kornick is a marketing executive, she starts dating him to help get Olivia an interview at his firm. Much to Chelsea's dismay, however, Tim is intensely sentimental and cries at the drop of a hat. As Olivia's interview process slowly progresses, Chelsea must figure out how to shake off Tim without insulting him or sabotaging Olivia's chances for her dream job.
Chelsea's father finally follows her advice to try dating again, but 'wingmen' Rick and Todd barely dare tell him he keeps falling for drag queens. Rick accidentally betrays to mortified Dee Dee that Chelsea confided into him her most embarrassing secret, sleeping with a comfort pillow she calls Mario Lopez. Rick gets his cousin, limo driver Brian, to arrange for the real Mario to pay her a visit, but her shame wins it from the hots for the Hollywood hottie.
When Chelsea meets Tommy Martinez, a hunky minor league baseball player who sweeps her off her feet, she finds herself feeling blissful and "exclusive," until he gets traded and called up to the dreaded Yankees. As part of a die-hard Red Sox family, Chelsea has to face her father's wrath and her own misgivings. Meanwhile, Rick continues to re-connect with Nikki, lending a helping hand with her grandmother.
Foppish talk from Chelsea helps Rick being delegated managerial duties by bar-owner Jerry. The staff however refuses to take his reasonable orders to cease theft and cheating seriously. When Jerry finds out, he fires Rick, so the guilty colleagues decide to stick with him and start heir own pop-up bar in Cheslea's apartment. Meanwhile Deedee is persuaded to join Nikki's 'corporal cleansing' Gwynneth Palthrow style, ignoring the truth, again recorded by Jerry's covert security cameras.
When Sloane takes everyone to a fancy French restaurant to say "thanks" for their support during her pregnancy, Chelsea meets the gorgeous and talented chef Robert, who begins courting her with sumptuous meals. As Chelsea becomes addicted to the rich, buttery food - shirking responsibilities and friendships - Olivia and Dee Dee realize that the only way to get her back may be an old-fashioned intervention.
Rick enters a cocktail competition, but the bar staff claims his recipes stand no chance, unlike Chelsea's bang bang. The price could kick-start Rick's lifelong dream, his own bar. Dee Dee's tutoring charity is Chelsea's easy way out when convicted to community service. Getting attached to her ghetto brat charge, she starts wondering whether its' a better cause for the small fortune she spent on fashionable boots.