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?

In this dramatic and heartfelt season finale, Jen is in hot water at her job selling scrubs and lotions, and as if that weren't enough pressure, her boss is also her boyfriend's mom…whom she lives with! Ryan knows that when it comes to business, financials always come before family. This means he has to do everything he can to turn Jen the caterpillar into Jenny the butterfly, all with very little time to complete the metamorphosis. But when it finally seems like he's getting her to open her up, Jen's past may shut down their hopes for good.