COVID-19 has affected not only current UCC students, but also our recent graduates in the Class of 2020. Some of them are taking a gap year, while others are all across the world experiencing different learning models and college lives. In this special issue of Convergence, we interviewed six Class of 2020 old boys currently in the UK, US, Ontario, Quebec, and BC. They described their unique experiences and provided valuable suggestions for current students. We also interviewed Mr. Borden - drawing on his recent experiences from his sabbatical, he leaves some very valuable advice for UCC students who might be thinking about a gap year.