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.
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.
When Dee Dee confesses to Chelsea and Olivia that she has a pillow named "Mario Lopez," Chelsea can't keep it a secret. Feeling badly about betraying her confidence, Chelsea tries to make it up to Dee Dee by arranging a meeting with the real Mario Lopez. Meanwhile, Melvin decides it might be time to date again. He enlists Rick and Todd to act as his wingmen and takes them to an interesting club where he has befriended one of the performers named "Sandy."
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.
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.
When Chelsea spies a pair of gorgeous but expensive boots in a shop window, she knows she must own them but is not sure how she will pay for them. Meanwhile, Rick is determined to win a local "mixology" contest and put the winnings toward starting his own bar. However, when the judges are less than impressed with his drink, he turns to Chelsea for the recipe to her delicious "bang bang" cocktail and promises to split the proceeds if they win.