Just After The Ending

Here is why Jesse became penniless without a home and no friends either. She needed to learn a lesson after her father Charlie Montgomery and his chauffer Wooddrow keep giving her tons of money and all she does is act wild in a crazy way including with that boy and she cares about no one but her own self and after finally landing in jail her Dad wished he never had a daughter and its granted and for Stella to learn that lesson, instead of money and things handed to her she has to work from scratch to earn her way.

Yes she did in many ways and it wasn't just the hard work in cleaning the house. She finally learned the value of earning money and when Stella and Marie and Nick made wishes all Stellas wish was, was that all of them get their wishes and when she cared for others and not herself at all Stella finally let her have her old life back. Then her father and Woodrow finally remembered her. Plus yes she kept her relationship with Chauffer Nick but Nick became a music composer as well.

However here is the factor at the end. Yes Jesse will no longer ask her Dad for handouts of his money and she will keep the maids job at the Starks Place until she gets another type of job later on and yes will also continue her relationship and true love with Nick and will never go back to her old ways at all.