I read a book that was published sometime around 2002-2005.  It was set in Webster Groves, Missouri (St Louis County).  I think it was a coming of age book about some boys around their senior year in high school.  I remember something about the flagpole at the high school.  I think it was written by a man.  I think it was set in the '70s but not sure about that.

In an even stranger twist, I think the author was from Milwaukee (where I live) and now lives in St Louis (or vice versa, but that's not written in stone).

I used to live in St Louis County and have a friend who lives in Webster Groves.  She wanted to know the title of the book when I told her about it.  I even emailed the Webster Groves library but got no response.  I guess they don't have a local authors selection. 

did you try google, with the info you have?