- „I'm sorry you miss how I looked at you. But I don't miss, how you never looked at me”
- —Henry to Jen[src]
Henry is a freshman football player who has a crush on Jen Lindley. He makes many attempts to persuade her to go on a date with him, and ultimately is successful. He is kind, sweet, gentle and has, as Jen describes him, this big, bleeding heart from which he pours out his emotions and she finds it incredibly intense at first, but also enormously impressive.
Henry starts Capeside High School as a freshman and a second stringer on the football team, but gets promoted when he brings Jack McPhee to the team and the two quickly become friends. Jack is also Henry's advisee on Jen, who Henry is completely lost in.
- Henry is the first freshman quarterback in the school's history.
- Michael Pitt stated about working with Michelle Williams, "I flew down there and she took me under her wing. [...] when I got down there, [Williams] did something that was really amazing. She drove me to the bookstore and she just went through the bookstore and said, 'You gotta read this, this, and this." 
- 2014 Elle interview
- where Pitt says a few words on DC...