1. The 40 Year Old Virgin (2005)
The Movie: The 40 Year Old Virgin is about... a 40 year old virgin portrayed by Steve Carell named Andy. As he opens up to some co- workers about his little secret, Andy feels mounting pressure to just lose it already! The 40 Year Old Virgin touched on societal pressures, male bonding, geekiness and love. Andy is satisfied collecting toys and being a little different and doesn't respond to meaningless sex the same way his male counterparts do. In the end, The 40 Year Old Virgin ended up being far more heart felt and wholesome than one could expect. The film ends with Andy professing his secret to a woman he loves and she...doesn't care. The film comments that it doesn't matter when we lose our virginity, just that we find a path to love. Follow your own path, not the one society deems "normal."
What It Says About You: Besides all the 40 Year Old Virgins out there, this film probably connected to a lot of people who just felt awkward around women and more comfortable at a Star Trek convention. This one being your favorite may say that you are a little socially awkward, but likable, a little shy with women or perhaps you've been through some bad break ups like Paul Rudd's character. At the end of the day, The 40 Year Old Virgin being your favorite Judd Apatow movie probably just says you've had more than one awkward relationship and just want to be accepted as who you are. Don't worry. Everybody finds their own Catherine Keener. Or maybe you just like Seth Rogen and jokes about 40 Year Old Virgins.