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 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".

Chelsea faces her father's wrath after the minor league baseball player she has been dating is traded to the Yankees.

When Sloane's husband calls to announce he is on his way home after she has spent the night drinking with her sister, it's up to Chelsea to get her cleaned up before he arrives.

Chelsea finds a pair of boots she wants but can't afford. Rick is determined to win a mixologist contest but needs a recipe from Chelsea.

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 Rick is promoted at the bar, his management style doesn't sit well with his co-workers; Nikki and Dee Dee go on a cleanse.

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 meets an attractive and talented chef who starts courting her with rich and sumptuous meals. Olivia tries to help Rick cope when it seems his girlfriend has moved on.

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.

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 Chelsea starts dating a sensitive customer to help Olivia get a job, she has to figure out how to cut him loose without hurting him....