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Chace Crawford - Source: TV2 -
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Chace Crawford looked like a "schoolboy" as he attempted to impress a waitress.
The Gossip Girl'star reportedly spent hours trying catch the eye of an employee at exclusive New York nightspot GoldBar, where he attended a birthday party.
"It was pretty funny. He was like a schoolboy looking to give the teacher an apple," an onlooker told the New York Post newspaper.
Crawford, 25, has recently said how starring in Gossip Girl has made him pay more attention to his appearance, and picked up a range of designer clothes so he looks more suave in public.
"Because of the success of the show, I've paid more attention to the way I dress and have developed my sense of style," he said.
"I like Ralph Lauren Rugby, John Varvatos - he's really bad-a*s - Diesel jeans, and I wear a slim-fitting, one-buttoned suit from Dolce and Gabbana. And I'm really getting into watches."
On the night Crawford was at GoldBar, the club was hosting a party for one of its doormen, Jonny Lennon, with guests also including Kanye West, Adrien Brody and Steve O from MTV show Jackass as well as members of rock group Kings Of Leon.