The Opposite Sex and How to Live with Them (1992)

Director: Matthew Meshekoff
Cast: Arye Gross, Courteney Cox, Jack Carter, Jensen Daggett, Julie Brown, Kevin Pollak, Kimberlin Brown, Mitchell Ryan

Synopsis:

Jewish Jack-the-lad David seriously fancies smart, rich Anglo-Saxon Carrie as soon as he first offends her in a Boston bar. They run into each other again and though she still says she finds him appalling he works on it and they are soon together. His even more reprehensible best mate and her blousy best friend watch bemused as the two fall deeply in love and then apparently as fatally out again