Bosom Buddies: Season 1

Friendship can be a real drag.

Kip and Henry work at an advertising agency as an artist and writer respectively. When the apartment that they were living in was condemned, they had no place to live. So Amy their co-worker, who has a crush on Henry, suggests that they stay with her but the only the problem is that it's for girls only. So they get into drag and assume the personas of Buffy and Hildegarde. When Kip meets Sonny, Amy's attractive roommate, he is smitten and when they learn that there's a vacancy in the building, Kip convinces Henry to take it so he can be close to Sonny, and so that this experience might be good material for a book that Henry can write.