|Full Name||Jacqueline Ames|
|AKA||Jackie; Miss Boss Lady (dubbed by Will)|
|First seen||Where There's a Will, There's a Way (Part 1)|
|Last seen||You've Got to Be a Football Hero|
As revealed in the second part of the fourth season premiere "Where There's A Will, There's A Way", Jackie was born and raised in West Philadelphia, in the same neighborhood Will was brought up in. She leaves West Philadelphia and moves to Bel-Air after accepting a basketball scholarship offered to her by the University of Los Angeles, which, coincidentally, is also Will's college of choice. She takes a job as store manager for the campus convenience store, The Peacock Stop, and hires Will as one of her employees when one of her workers quits and conveniently leaves a vacant position for the desperate Will.
Because the two of them grew up together, Will and Jackie are often shown to have been extremely close and know each other very well. Will recalls in one episode that Jackie was a terrific runner, as she was able to beat anyone on the playground in a foot race when they were younger. Jackie also seems to have learned to play basketball from Will, as she mentions in the same episode that Will was the one who taught her how to do a proper jump shot. Although Jackie claims that she and Will were "just friends", Will revokes this statement by reminding her of their little tryst after one of their friends' parties, implying that they were romantically involved once back in Philly. They seemed to have lost touch with each other after Will left for Bel-Air, which Jackie was initially upset about and caused her to slap Will in the face when they encountered each other for the first time in three years after Will's departure from Philly. She eventually forgives him when he tells her that the reason he didn't call was because he missed her too much, and they resume their friendship after their reconciliation.