Are You There, Chelsea? - 1 ª Season

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.

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