Being Erica (2009)

"Therapist" Dr. Tom - who is constantly spouting famous and not so famous historical quotes - is Erica Strange's savior and worst enemy. Erica, a young adult woman, is having a bad life because of the bad decisions she's made.

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Being Erica Season 1, Episode 9: Everything She Wants
Erica travels back to December 1999, when her best friend was a lesbian.