Modernizing perspectives on roommate compatibility might be one way that administrators reinforce the value of the roommate experience in contemporary campus housing. Using the insights of a study published by Hallisey, Harren, and Caple in "Journal of College and University Student Housing" in 1980 as a springboard, this article will contrast the assumptions of living on campus yesterday and today with specific focus on changing generational expectations about housing amenities, shifting ideas about roommate matching, evolving perspectives on diversity in housing, and an increasing focus on conflict management in an environment of diversity and social media. [For reprint of "Roommate Changes in Residence Halls: Can They Be Predicted?," see EJ1093926.]