William is a playboy executive who doesn’t take his job at his father’s development firm seriously. Pops tells his numbskull son to shape up and orders him to hire an attorney to help him learn the family business he’s spent a couple of decades ignoring.
William ditches the interviews his father has lined up and dashes outside for a coffee break. While waiting for his java, an attractive woman who happens to be an attorney harangues him about destroying her family’s restaurant.
Despite having no clue what she’s talking about, William says he’ll help if she pretends to be his lawyer for a week, just long enough to convince his dad he’s taking the job more seriously (nothing says sincerity more than a fake relationship).
Annie, who specializes in family law, goes along with the gag but forgets to get his commitment in writing. She ditches her clients for the week (Those pesky adoption hearings can easily be rescheduled for the new year. What’s one more Christmas in a dreary foster home?) to cavort around Chicago with William and plan some sort of holiday gala that is intended to show his father he’s taking the development business seriously.
The party is a bust, and William’s dad finds out he’s been goofing off all week and Annie’s just pretending to be his attorney. As if that weren’t bad enough, William’s half-hearted attempt to convince his dad to spare Annie’s family restaurant fails.
With only one commercial break left, William leaps into action. He figures out Annie’s parents’ building qualifies for historic preservation status and thwarts his dad. This somehow impresses his father and Annie, and both forgive him.
Relationship update: A whirlwind romance goes down the tubes three weeks later when Annie realizes William’s irresponsibility isn’t as endearing as her parents seemed to think.
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Edits by Todd 