TV-PG-L. Emma has built a successful lifestyle website that she puts her heart and soul into called “Classically Emma”. But when her numbers start trending down, she thinks she might’ve found her fix in a partnership with an ambitious millennial named Jill who has her own dreams. Will Jill’s protective brother Jesse become a roadblock on Emma’s path to lasting success? Or will he be the unexpected obstacle that leads her down an even better road?