The Fresh Prince Of Bel-Air: Take My Cousin Please
Series 4 episode 11 from 1993.
Will is struggling at school and is on academic probation.
His teacher’s wife has left him and the grades have gone down as he takes out his anger out on the students.
Will sets him up with Hilary, thinking he’ll now get better marks.
It all goes downhill but then, right at the end, Hilary confesses she actually likes him.
Movie pages here.