There's real-life serendipity and then there's Hollywood serendipity. Real-life serendipity involves running into a friend or a high school chum on vacation and then remembering how you used to discuss trigonometry while standing at the urinal. It's not phenomenally interesting. Hollywood serendipity involves every single object of significance reappearing throughout a movie at exactly the perfect moment and guaranteed to convince a character of something vitally important to their lives.
This stupidity combines with a faith in the power of fate, held by a perky British lass named Sara (Kate Beckinsale). She meets Jonathan (John Cusack) in Macy's when they both grab for the same pair of gloves. They have coffee and are instantly in love. The second the whacked Sara started talking about her belief in the power of fate, Jonathan should have immediately thought to himself, "psycho alert!" and dashed for the exit the next time she went to the bathroom or glanced at her shoes. Instead, he falls in love and spends the next several years trying to hunt down a used copy of "Love in the Time of Cholera" that has Sara's phone number in it. See, when Sara tries to hand him her number on a piece of paper, some wind blows it out of his hand. She sees this as a sign and writes her number in a copy of the book, which she sells to a used book store. She tells Jonathan that if they're meant to meet, he'll find the book. If Jonathan had any self-respect at all he would have held up his middle finger and said, "Here's a sign for you."
Jonathan writes his name and number on a five dollar bill. Then they both enter separate elevators in a hotel. Again, Sara says that if they both end up on the same floor, it'll be fate's choice. Just how many "signs" does a desperate guy need to tell him that a woman is out of her mind? You know, I like to imagine British women screaming out my name during the throes of lovemaking as much as the next guy, but Sara seems a lot more likely to be running around chasing the cats with a butcher knife because little voices in her head tell her that Satan meows.
You can bet that Jonathan and Sara eventually meet again because all these ridiculous signs finally come together. Naturally, each has a faithful, skeptical friend who's along for the ride. Jonathan has Jeremy Piven and Sara has Molly Shannon. They run around together going in used book stores and looking at the back of every five-dollar bill. Any real male friend would have punched Jonathan in the face after about five minutes of his whining, especially since years later he gets engaged to another stunningly beautiful model. Oh, you're screwing a beautiful model but you're still in love with this other beautiful model who you want me to help you locate? Answer: Clip the hairs off my scrotum with your teeth, you self-obsessed prick.
The bottom line: Any man with a brain would have called Sara on her spiritual idiocy within two minutes. Anyone who wouldn't deserves whatever cruel tricks fate might play on him and as we all know, those tricks usually involve venereal disease and drunken stupors, not getting the girl in the end.
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