His first date was in eigth grade. He had this relationship over the phone all summer with this Spanish girl named Cessi. They went out to the movies when she came back. He had a light blue turtleneck which he thought was cool back then. Then when he saw Cessi he was petrified and couldn't even look at her in the eye, let alone talk to her. They saw "When Harry Met Sally" and he couldn't move. Then afterward, they at French dip sandwiches. Cessi was really shy and finally said "Do you have a problem with me eating this sandwich?" and he said, "No, no, not at all." He acted really weird throughout the whole date which was their last date. Leo liked her for another year but was so mortified he wouldn't go near her.
His first kiss wasn't much better. He was in ninth grade and the girl gave him a ton of saliva. He said he had to spit it all out when she left.
But do not worry, he's a whole lot cooler with dates now. He's been seen with Bridget Hall, the tall Ralph Lauren Polo supermodel. Then in 1994 he ran around town with actress Juliette Lewis. Next came Alicia Silverstone and Liv Tyler. Then he drooled over model Bijou Phillips. But just when the relationship was getting hot, he took Kristine Zhang to the premiere of Romeo and Juliet. However he says they're all just "friends". Right now though, there's a mysterious girl he's fallen madly in love with but she's not in the acting biz.
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