YMMV / Transparent

• Harsher in Hindsight: In the second episode, Maura is warned that none of her family will still be around her in five years. When the show was renewed for a fifth season, Jeffrey Tambor himself was fired for sexual harassment, which resulted in the production team having to work around his absence by instead concluding the series with the Finale Movie Musicale Finale and killing off Maura Pfefferman in it.
• Heartwarming in Hindsight: A flashback to Maura's birth has her father assuming that his new child will be a daughter and claiming he knows these things as a father, which becomes a lot more endearing in retrospect when the fourth season has Maura reunite with her father and Moshe Pfefferman is shown to be okay with Maura being trans.
• Jerkass Woobie: Depending on your feelings about them, Sarah, Josh, Ali, and/or Shelly could count. All have their moments of rudeness and selfishness, and all of them are deeply lonely and smarting from the emotional wounds they've inflicted on each other.
• Overshadowed by Controversy: While the show was well-received, there were some complaints from trans activists early on about yet another cisgender man taking a role of a transgender woman. However, that paled in comparison to when Jeffrey Tambor was accused of sexual harassment by multiple trans women working on the show.
• The Woobie: The whole Pfefferman clan qualifies.
  • Maura. The flashbacks reveal her unhappiness before coming out, and her transition to womanhood isn't any easier.
  • Shelly. While she hides it by being Deadpan Snarker, she's ultimately frustrated and lonely, especially since her second husband, Ed, is dying and her kids hardly ever come to visit her. Later episodes also show that Shelly was/is deeply hurt by Maura not being happy with her, and when she tries to rekindle their former relationship after Ed's death, only for Maura to walk out on her, it's incredibly sad.
  • Sarah. While she's seemingly the most stable of her siblings, it becomes rapidly clearer that she's not happy with either of her relationships and that she doesn't really have a firm handle on her emotions.
    • Though she comes off more as a Jerkass Woobie or an outright Jerkass, since she's very hedonistic and uncaring of anybody's feelings but her own.
  • Josh. He goes from relationship to relationship without really settling down, and when he finally finds someone he really loves Ali messes it up by telling her that Josh has a messed up relationship with women.
  • Ally. She's completely directionless, which may or may not be the result of her upbringing. She later feels betrayed by her family when she finds out that Josh has been sleeping with her best friend and that Maura may have agreed to cancel her Bat Mitzvah to go to a cross dressing camp.
  • Raquel is Adorkable and genuinely nice, but also deeply insecure and afraid of rejection. When she gets together with Josh, the Pfeffermans' many personal dramas start impinging on her life all at once, to the point where she's frequently disheveled and on the verge of tears. And then the miscarriage happens.

---