I saw Caroline Kennedy once while I was living in New York. I was just walking down the street and she walked past me. I then became a stalker, turned around and followed her to see if it was really her. She wasn't with anyone and she walked into a private school to pick up her kid. It was somewhere around Amsterdam and 72nd.
This experience wasn't as memorable as seeing Angelina Jolie. It was Fall of 2004 and it was around the time "Mr and Mrs. Smith" must have been filming, so Angelina was at the absolute Zenith of her hotness. I wasn't one who thought Angelina was hot before this encounter (couldn't get past her former goth phase), but she was the most beautiful woman I've ever seen in person in my lifetime. I was disappointed to see that she's recently turned into a skeleton when I watched "Wanted."
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