#7: PRETTY WOMAN (1990)

Sexual Arrangement: A rich businessman hires a prostitute to be his escort for a week of business and social events.

Admittedly, we’ve signed up for a few online dating sites during our past dry spells, but none of the subsequent dinner partners looked anything like Julia Roberts. One resembled Eric Roberts, but let’s forge ahead, shall we? With money to blow, Richard Gere’s millionaire character compensates for his single status by paying Roberts’ hooker-with-a-heart-of-gold to act as his stand-in girlfriend. In true romantic comedy fashion, they fall in love and live happily ever after, debunking that age-old piece of West Coast hip-hop wisdom: “You can’t turn a ho into a housewife.”