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.
Filming took 20 days.
The Howie/Marshall storyline is semi-autobiographical to a relationship writer/director Greg Berlanti had.