The Ugliest Girl in Town

The Ugliest Girl in Town is a short-lived American sitcom produced by Screen Gems for ABC.  It ran from September 26th, 1968 to January 30th, 1969.

Timothy Blair is a Hollywood talent agent.  He falls in love with Julie Renfield, a British actress who is visiting the United States to do a movie.  After that movie is finished, she returns to England.  To assist his brother Gene complete a photography assignment, Timothy dresses as a hippie and poses for a photo shoot.  The photos are sent to a modeling agent in England who assumes that they are of a woman.  He offers “her” a job.
Knowing that this would be the only chance to go to Great Britain and be with Julie, Tim accepts and dubs himself “Timmie”. Tim has two weeks of vacation to spend as much time with Julie as he can, but when as he is about to leave with his brother, Gene loses £11,000 gambling.  Unless he pays him back, Tim has to continue being Timmie for a while longer.