After personal assistant Kiersten Abbott wins sixty-nine million dollars in the lotto, she suddenly has more than enough money to quit her impossibly demanding job. But where's the fun in that? She decides to stay and exact a little revenge on her insufferable ass of a boss. Billionaire Cole Harrington quickly figures out something's afoot with his usually agreeable personal assistant. When he finds out about the office pool betting on how long it'll take him to fire her, he decides to spice things up and see how far he can push her until she quits. The game is on, with everyone waiting to see who will crack first. But the bet sparks a new dynamic between them, and soon they realize they just might have crossed that fine line between hate and love.