#5: THE 40-YEAR-OLD VIRGIN (2005)

Sexual Arrangement: Waiting until the 20th date to have sex for the first time.

Brace yourselves for a truly world-shattering thought. Are you ready? Here goes: It’s better to delay sex if you really want to get to know a girl. As blasphemous as that sounds, it’s true. Take the budding relationship between Steve Carell’s inexperienced dater and Catherine Keener’s single mother in Judd Apatow’s hilarious The 40-Year-Old Virgin. Having never laid the pipe, the middle-aged Carell fears that misfiring beneath the sheets could ruin a good thing, so he manages to push sex back 20 dates. In turn, he and Keener are able to fall for each other’s actual person and not simply what’s under their respective belts. And that, wannabe gigolos, is how it should be done. Sadly, one night stands don’t qualify as meaningful relationships.