Annie is 27 years old and has taken a break from medical school to waitress, make money, and pay down her crushing student debt. She is also a drinker. Deeply shaken by what she sees as her many failures, she speaks to her doctor who diagnoses depression and recommends volunteering to get out of her own mind. On a volunteer beach clean-up, she meets Dean, a smart, funny, sexy fireman, whose only noticeable vice is cheesecake.
Dean proposes but Annie asks for more time. He is angry and hurt. She has hidden her affair with alcohol and needs time to reduce her gray-area drinking.
Immediately after his proposal, Annie gets a distressed call from her estranged mother. This phone call launches a grueling, four-day road trip with her mother, her loving but clinically depressed stepfather, and a tranquilized cat. On this arduous journey, Annie begins to understand the family trauma behind her drinking habit. Sober curious, she stumbles on her way to moderation but continues to get up and try again.
