When Timothy Olyphant and 'Andrew Keegan' were filming their scene on the park swings, a group of teenage girls noticed Andrew and waited until the scene was over to ask him for his autograph. When Timothy offered his autograph, the girls declined as they didn't know who he was.
As Greg Berlanti was a writer/producer of the series Dawson's Creek, he showed the script for this movie to one of his favorite actors Kerr Smith who was part of the Dawson's Creek cast. Kerr loved the script so much that he agreed to cameo any role Greg offered.
Greg Berlanti originally turned down the role of director, and he said in interviews that the studio offered the director position to him at least three times because they couldn't find the right director. By the fourth or fifth time they'd asked him, he accepted.