Glen or Glenda

A character runs into an old friend who, unbeknownst to them, has transitioned from male to female.

Night Court

Appearances

• WKRP in Cincinnati: Season 3, episode 5, "Hotel Oceanview" (1980). While Herb is on a business trip in Dayton, a beautiful woman named Nikki, who claims to be an old high school classmate of his, invites him back to her hotel room. While they're fooling around on the bed, Nikki confesses that when she knew Herb in high school, she was presenting as male.
• Night Court: Season 3, episode 6, "Best of Friends" (1985). Dan's best friend from college, Chip, comes to visit, and Dan is shocked to see that Chip has transitioned and is now living as a woman.
• It's a Living: Season 3, episode 12, "Gender Gap" (1986). An attractive woman customer named Louise starts getting close to Sonny, and Nancy thinks she looks familiar but can't remember who she is. Eventually, Louise reveals to Nancy that when they met many years ago, she was living as a man, and she started her transition the very next day.
• Just Shoot Me!: Season 5, episode 6, "Brandi, You're a Fine Girl" (2000). Finch's childhood best friend, Burt, is in town, and he can't wait to catch up. When he goes to the bar to meet Burt, he runs into a beautiful woman, who tells him she's Burt. At first, Finch is shellshocked, but soon he starts to develop an awkward crush on his old buddy.