Night Court did the same thing. The assistant D.A., Dan, has an old buddy who visits after many years and turns out they transitioned and have a boyfriend. Dan is stunned because they used to party and womanize together, but his friend said he was never actually into it. At one point Dan argues with the new boyfriend and says, “He used to be a guy!” Boyfriend says it doesn’t matter. He loves her. That episode really stuck with me, watching it as a kid.