Jill is hanging on by a thread at her dress sales job, and her boss Jacqueline isn't budging an inch. Thankfully Jill's called Ryan, who's willing to trade in his signature suit for a prom dress in order to spark her passion for fashion. Now he has just five days to get Jill at Maddie's level, who is a sequin-selling superstar and averages four times the commissions as Jill. Can Ryan boost her performance quickly, or will Jill's hopes of keeping her job completely unravel?