Character Analysis
Mr. Howard is Jack's possible salvation: an alumni of Hill who seems really excited by Jack's interest in the school:
He seemed to get younger and younger, as if talking about being a boy had changed him into one. (29.1)
Like Sister James, he appears as a positive influence in Jack's life… and even feeds on Jack's phony stories. He also gives Jack a much-needed out from any expectations.
I shouldn't be afraid of disappointing him or letting him down in any way. (29.10)
That may signal a real change in Jack's life. After all the "you're not good enough" from Dwight, here's somebody who's actually going to forgive him if he falls. It may not change the failure, but it might help give Jack a better sense of self-worth.