After receiving a D.U.I., Chelsea Newman decides it's time to change her life starting with moving into an apartment closer to her workplace, so Chelsea and her best friend Olivia move into the same apartment building their co-worker Rick lives in. Meanwhile, Chelsea's sister Sloane is due to give birth and is unsure if Chelsea will be there for her.

When Sloane's high school boyfriend shows up at the bar, Chelsea can't resist going out with him; Rick tracks down his ex and finds out she is engaged.

When Sloane plans a social gathering for her church group at Jerry’s Ultimate Sports Bar, Chelsea finds herself attracted to the band’s cute lead singer Luke but his virginal ways soon become an insurmountable obstacle. She then decides he is the perfect match for Dee Dee and sets about matchmaking. Meanwhile, Rick’s old girlfriend Nikki takes a job at the bar and while Rick is excited to have her around, her saucy personality doesn’t sit well with everyone.

When Nikki's (Natasha Leggero) fiance Elliot (P.J. Byrne) gets cold feet, Chelsea, Olivia and Dee Dee come together to help her look good for him. However, when the plan breaks down, Chelsea realizes she might be stuck with Nikki for a bit longer than she anticipated. Meanwhile, Chelsea has also taken in another stray, in the form of a dog named "Andy Dick," and she realizes she's got to find the pet a good home as well.

Chelsea accepts an invitation to go deep sea fishing with her new doctor, Dr. Thomas (Tom Parker), and his partner, Dr. Rosen (Josh Meyers), and brings Nikki and Dee Dee along for the trip. As Dee Dee hits it off with Captain Steve (Nate Torrence), Nikki and Chelsea plot to pair off with the eligible doctors, but the girls are in for a surprise when it becomes apparent the doctors are more than just business partners.