My Lady Boss (2013)

Zach is a rich boy forced to find and keep a job after a major blunder in a company he set up. He ends up working for ­Evelyn, whom he discovers to be the boss from hell. In the long run, he sees her for who and what she really is. Meanwhile, Evelyn is an uptight and tough Brand Manager who hires an assistant Brand Manager. When she finds herself dumped by her boyfriend, Evelyn seeks comfort in Zach, her assistant who shows a different side of him. As they get to know each other more and as their encounters become more intimate, they begin to ask themselves if what they feel for each other is for real. The problem is romance between boss and subordinate in a company is not allowed. Things get complicated when an office romance develops between the unlikely pair.

Unfortunately the movie My Lady Boss is not yet available on HBO Max.