A Crazy Bet Turns His World Upside Down… Megan Winston is out of money and needs a big break to keep her father’s coffee shop open. Her new landlord, Bryant Stanley, wants a break from being set up on dates after his failed engagement. An ambush from Bryant’s mother leads to an insane bet. Megan will be Bryant's fake date, but if he dumps her before three dates are over, she gets a year of free rent. Bryant: I never lose in business, and I won’t start now. Megan: I’ll embarrass this billionaire into dumping me. From a feathery chicken suit to a surprise fake engagement, I won’t stop until I’m the winner.