The Outcast (ST:TNG episode)

The Outcast is one of the few Star Trek episodes to deal with queer issues. Will Riker falls in love with Soren, a member of a more-or-less androgynous species that disapproves of overt masculinity/femininity. Soren is forced to undergo a sort of reparative therapy to eliminate tendencies towards femininity.

Jonathan Frakes, who played Riker on the series, wanted the episode to feature the queer angle more, and do a better job of it. Frakes has said that the actor to play Soren should have been male, and presented more masculinely, and also thought the episode didn't go far enough in raising the issue.