Max Sagan's mouth is always getting him in trouble. His special talent for saying the wrong thing at the wrong time to the wrong person makes it hard to hold onto either a job or a boyfriend for long. When Max is fired yet again, his best friend Noah reluctantly gets Max an interview where he works. Max is grateful, but unsure if a party boy like him will fit in at a stuffy law firm. Then he meets Noah's gorgeous boss, lawyer Owen Hart, and becomes determined to keep this job. Others say Owen is far too professional to date an employee, but Max has a plan — keep his fingers crossed, look cute, and hope it works out. Meanwhile he's working hard to keep his big mouth shut so he might last an unprecedented entire month at his new job — long enough, he hopes, to catch Owen's eye.