It's hard not to notice how attitudes around sexual orientation and gender identity (SOGI) have changed over the past two decades. In this article, Stewart Rudy compares his time as a public school student to his time as a public school educator. Rudy questions whether improvement in the school system has translated into improved experiences for students as they navigate issues of SOGI in the school environment. The reflections shared here are based on personal experience and are also informed by discussions with several colleages at Stewart's workplace, a high school in Philadelphia.