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Currently you are able to watch "The Many Loves of Dobie Gillis - Season 1" streaming on Plex for free.
The Many Loves of Dobie Gillis is available to watch for free today. If you are in India, you can:
In Season One, we meet Dobie Gillis (Dwayne Hickman), who is obsessed with impressing and winning over the girl of his dreams, the beautiful Thalia Menninger (Tuesday Weld).