A marketing executive and a fashion/advice journalist get wrapped up in coinciding bets. He must make a woman fall in love with him in just 10 days; she has to get involved with a man, then get him to dump her in order to inspire her for a column.

Classic! This movie has stood the test of time. It’s hilarious! It’s good if you are dating. It’s good if you are married. It’s good if you have ever dated, or ever been married. Some of my favorite parts: the love fern, a fake vegetarian, a fake therapist, 15 messages on the answering machine (remember those?), and McConnaughey’s motorcycle.

There are some very important lessons to be learned here: All women can act a little crazy, if you find one that is mostly not crazy – hold onto her. Also, if you want to get a chick to stick around, let her meet your family. Finally, a man might be clever enough to trick a woman for like a week… but will never really come out on top.

Warning: You will like it better if you stop right after they start to fall in love for real. It goes downhill pretty quick after that.