Are You There, Chelsea? - Season 1 (2012)

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.

Chelsea brings Dee Dee and Nikki along with her on a deep sea fishing trip she was invited to go on.

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.

Chelsea's plans to throw a surprise birthday party to Sloane take an interesting turn when Sloane's husband phones Chelsea to tell her that he's on his way back home. Rick has some mixed feelings about a dream he had of Chelsea.