My Chauffeur is a delightfully funny romantic-comedy about a female chauffeur trying to make her mark on an all-male limousine company called Brentwood. Casey Meadows begins her job at the service company as a driver, who is assigned to drive, Mr. Witherspoon. Regardless of how well she accomplishes her job she is greeted with sarcasm and snide comments from some of the other drivers. Giles, Mr. Witherspoon's Butler, is especially difficult to deal with and reports her to McBride, her boss.
Casey does not, however, lose face and continue to arrive on the job daily in a multitude of kooky ensembles fighting back against these men. It is her quick wit and cunningness that drive Giles to the brink. As Mr. Witherspoon's chauffeur, Casey is also responsible for driving around his son, Battle who is equally misogynistic as the others. Battle is a power-hungry workaholic who could not care less what any woman has to say.
Through a series of misfortunes, Casey and Battle end up stranded in the middle of nowhere after the limousine breaks down. Battle angry begins to snap and take it out on Casey for being an incompetent driver. They begin to walk to their destination in the blistering heat, as Battle is determined he will arrive where he is expected. However, his stubbornness gives way as he becomes intrigued by Casey's ability to persevere in the most unfavorable of circumstances. Casey and Battle fall madly in love during their journey back to the Witherspoon house.
Upon their arrival at the Witherspoon home, the two explain to Mr. Witherspoon that they are in love and have decided to get married. This announcement is foiled as Mr. Witherspoon realizes who Casey's mother is and tells her that it is possible that he may also be her father. Luckily, Giles, an unwilling adversary comes forward in order to set the record straight.