When party girl Chelsea finds herself in jail with a DUI charge after a crazy night out, she turns to the one who's always been there for her: vodka. She prays to vodka, confessing that she knows she's messed up, but if by some miracle she gets out of jail, she'll promise to turn her life around.
Apparently, vodka heard her prayers because, moments later, Chelsea is bailed out by her sister, Sloane. Sloane is very pregnant and very frustrated with her sister's antics. Chelsea isn't the only one affected by her drinking; with her husband in Afghanistan, who's supposed to drive Sloane to the hospital when the baby comes now that Chelsea has a DUI?
At her job bartending at Jerry's Ultimate Sports Bar, Chelsea is mocked by her boss, Rick, for getting a DUI. Chelsea's friend and co-worker, Olivia, comes to her defense; she's had Chelsea's back since grade school.
When Rick explains that there's a girl in his apartment looking for roommates, Chelsea senses an opportunity. Rick lives just a block from work... if she lived in this apartment, she'd be able to keep drinking, without having to drive!
Chelsea and Olivia go to check out the apartment and are met by a very strange tenant. Dee Dee is sweet, chaste and charmingly odd, telling Chelsea and Olivia that they'll have to wait until the bachelor hands out the final rose to talk about the apartment. But despite her strange mannerisms, the apartment IS pretty awesome, and Chelsea and Olivia decide to go for it.
Later, at the bar, Chelsea's startled by the fiery red hair on one of Rick's friends. But when he orders her drink (vodka and more vodka), she realizes that maybe she shouldn't have written him off so quickly. Chelsea chats it up with Jonathan and comes to find that he's actually a very cool guy; the two make plans to go on a date.
When Chelsea and Olivia move into the apartment, Chelsea brings along her appropriately named cat, Assface. Dee Dee immediately takes a liking to him, even though he viciously scratches Dee Dee across the neck. It's just because Assface is mad he can't talk!
Sloane arrives to go to lamaz class with Chelsea, only to find that Chelsea's forgotten and has to work. Sloane's frustration with Chelsea's behavior has hit its peak; how does she even plan on getting Sloane to the hospital? When Chelsea counters with more sarcasm, Sloane tells her she's had it with her behavior. She tells Chelsea not to bother showing up when the baby comes.
Chelsea works out her frustration with Sloane the best way she knows how: hooking up with Jonathan. Chelsea thinks she's gotten past his ridiculous red hair... until she sees what he has going on downstairs. Chelsea's saved by the phone when her dad calls: Sloane's in labor, and she's got to hightail it to the hospital.
Once Chelsea arrives, their argument from before just seems petty. Chelsea's there for Sloane and sticks with her until the end. After the baby's born, Sloane tells Chelsea that she's decided to name the baby Sylvia, after their mother.