A self-loathing, alcoholic writer attempts to repair his damaged relationships with his daughter and her mother while combating sex addiction, a budding drug problem, and the seeming inability to avoid making bad decisions.
Although she has traveled all over the world, flight attendant Montana Moore has yet to find a man with whom she wants to settle down. However, with her sister's upcoming wedding and pressure from her oft-married mother, she's determined to get engaged in the next 30 days. In that time, her best friends (and fellow flight attendants) conspire to help her re-encounter her exes as she flies all over the country.
Thirty-something Elizabeth must decide whether to salvage her disappointing relationship with Drew. Meanwhile, Bea, a worrisome teenager, reconnects with her introverted childhood friend, Andy, at their high school prom. Past and present collide as two couples explore love over the course of one night at a hotel.
