A random collection of films authored by or about my transgender, intersex sisters, and gender-nonconforming persons all over the world. I watched some of them, and I was inspired by some of them. I met some of the authors and heroines, some of them are my best friends, and I had the pleasure and honor of interviewing some of them. If you know of any transgender documentary that I have not covered yet, please let me know.

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Bittersweet Becoming

Director: Polina Teif
Release Year: 2023

Synopsis:
"Bittersweet Becoming", directed by Polina Teif, offers an intimate and poignant portrait of Karla Rae James, a trans woman navigating the complexities of a late-life transition. Set in Toronto, this deeply personal documentary invites viewers to witness Karla’s journey as she embraces her true identity in her 60s, defying societal expectations and the passage of time.
 
The film captures her resilience, vulnerability, and the bittersweet moments of reclaiming oneself at an age when most are focused on retirement and legacy. Karla Rae James is a lively, spirited trans woman who has spent much of her life suppressing her authentic self due to familial and societal pressures. Having taken on roles dictated by others, Karla only fully embraces her gender identity as she approaches her seventh decade. After caring for her ailing mother, Karla returns to Toronto with not just an inheritance, but her mother’s blessing to pursue a long-delayed transition on her own terms. This new chapter represents a chance to finish what she began years ago—a late-life transformation, full of both triumph and challenges, that comes after years of waiting for the right moment. "Bittersweet Becoming" chronicles the final phase of Karla’s transition, which she had put on hold for decades. The documentary goes beyond the external changes Karla undergoes; it captures her internal evolution, her reflections on life, and her hopes for the future.
 
The film offers rare and unfiltered access to Karla’s experiences, from her reflections on the past to her fears and desires as she undergoes gender-affirming surgeries. We see a woman who is determined to live authentically, no matter the obstacles, a person whose capacity for kindness and introspection leaves an indelible mark on those she encounters. Director Polina Teif’s connection with Karla is central to the film’s success. Teif, who spent three years filming and building a rapport with Karla, treats her subject with a profound level of care, empathy, and sensitivity. The trust between the filmmaker and the protagonist is palpable, allowing Karla’s humanity to shine through the lens. Through this close relationship, the documentary unfolds not only as a portrayal of one person’s transition but also as a celebration of the resilience of the human spirit. Karla’s journey is filled with both heartbreak and joy, yet her unwavering courage is evident at every step, providing a profound sense of hope for those who are still searching for the courage to be their true selves, regardless of age or circumstance. At its heart, "Bittersweet Becoming" stands as a powerful reminder that it is never too late to live authentically and reclaim one's identity. Karla Rae James emerges as a deeply inspiring figure, not only for trans individuals but for anyone who has ever struggled to live in alignment with their true self. Her strength, wisdom, and open-heartedness offer a rich lesson in self-acceptance, proving that the quest for authenticity knows no age limit.
 
In her interview for the Stephanie Stevens Show, we can hear that Karla’s transition wasn’t a linear process, but rather a journey of discovery. She began by living in the gay community before gradually embracing a more trans identity. “I lived for a while as a gay male,” she shares. “Then, I slowly became more trans, more trans, until that’s who I became.” For Karla, the journey toward embracing her authentic self was deeply personal, and it took time for her to find the courage to seek medical support for her transition. “Finding a doctor to talk to was difficult,” she admits, “I went through five doctors before I could even get the words out.” It wasn’t until she was already living as a woman that she was able to speak openly about hormone replacement therapy. But once she made that decision, she did so with confidence, knowing that living authentically was the only way forward. Karla’s path to self-realization and empowerment was influenced by iconic figures like Jackie Shane, a pioneering trans woman and performer. During the 60s and 70s, Jackie Shane made waves as one of the first trans women to perform publicly in a world that was largely unwelcoming to those who did not conform to societal expectations. For Karla, Jackie’s boldness and resilience provided a template for how to live openly and unapologetically. Karla’s message to younger generations of trans women is clear: don’t forget the trailblazers who fought for the rights and visibility that are now taken for granted. “Don’t forget about us,” she says, referring to older trans women who have fought for the community’s rights. “We’ve been here all along, and our needs are just as important as those of the younger women.” She advocates for unity within the community and calls for more support for elderly trans women, whose struggles are often overlooked.
 
Polina Teif, the filmmaker behind this poignant documentary, has a strong background in both visual arts and documentary filmmaking. Born in Minsk in 1989, Teif now resides and works in Toronto. Her academic journey included studies in Visual Studies and Semiotics at the University of Toronto and Documentary Film Production at York University. Her previous works, such as "Eulogy for the Dead Sea" (2022), have already garnered attention for their thoughtful exploration of personal and collective histories. In 2019, Teif won the Hot Docs Pitch Prize and the Planet in Focus Green Pitch Award, and the following year, she participated in both the EMF DocSalon and the Hot Docs Accelerator Program at the Berlin International Film Festival. With "Bittersweet Becoming", Teif cements her reputation as a director who approaches sensitive subjects with both depth and humanity. In conclusion, "Bittersweet Becoming" is more than just a documentary about transition. It is a celebration of one woman’s determination to live fully, unapologetically, and on her own terms. Through Karla’s story, Polina Teif presents a universal tale of self-discovery and acceptance that resonates deeply with all viewers, regardless of their background or experience. The film serves as a reminder that it’s never too late to embrace who we truly are, and that the journey to self-actualization is always worth it, no matter when it begins.
 
via: youtube
Image credits: YouTube

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