For those interested in James' book/lecture series *Pragmatism*, it turns out that Dewey was in the audience for the third lecture at Columbia (at Teacher's College). From a letter (1907.02.01): William James to Alice Howe Gibbens James:
Wm. James: "Yesterday [31 January], my third lecture was read to an audience hardly diminished.1 Certainly well over 900, & sounded well--to me. We, i.e. Cattell, Dewey, Miller, Woodbridge, Strong, Marshall, and others beside myself adjourned to the Faculty Club and had a hot & heavy and (I think) in-||structive pragmatism discussion with dinner at 8, until ½ nine, when I left & came to bed."
NOTE: 1. Possibly at Harvard Club, 27 W. 44th St., New York.
Richardson has some nice details on this, too: here.
Thanks to Larry Hickman of the Dewey center for pointing this out.