Upon returning to the United States, Bob attended DeMatha High School in Hyattsville, Maryland, graduating in 1971, and then went on to Georgetown University, where he pursued a double major in philosophy and psychology, receiving his Bachelor of Arts degree in philosophy in 1975.

[4] In 1986, Bates and a friend, David Wilt, who he knew because they sang in the same choir, the Alexandria Harmonizers, started the company Challenge, Inc. to explore the possibilities of creating interactive fiction games.

Games designed by Bates for Legend included Timequest, Eric the Unready, and John Saul's Blackstone Chronicles.

[3] In 2017, Bates launched a Kickstarter for his game Thaumistry: In Charm’s Way,[8] which was successfully funded having raised $35,238 from 1,053 backers.

[9] In the course of his career since 1986, Bates has written, designed, produced, or overseen more than 45 games,[6] with over six million units sold.

[10] He has twice been Chairperson of the International Game Developers Association in 2005 and 2009, and has served on the advisory board of GDC Europe.