YouTube: Chloe Pickard

Show: Chloe Pickard (YouTube)
Episode: Single, Alone and Sad: Transgender Woman Dating
Release Year: 2021

Chloe Pickard, an Australian YouTube vlogger, is known for her raw and authentic content, often discussing personal experiences and emotions with her audience. One of her most poignant and vulnerable videos, titled "Single, Alone and Sad: Transgender Woman Dating," aired on February 27, 2021. In this video, Chloe opens up about the challenges and emotional turmoil that come with dating as a transgender woman, as well as the deeper issues of self-worth, trauma, and the fear of rejection.

 

Chloe begins her video with a seemingly lighthearted tone, initially intending to share a fun and positive dating story. However, as she attempts to record, emotions overwhelm her, and she is overcome with tears. This emotional shift becomes the catalyst for a far more personal discussion about her internal struggles. Chloe reflects on how she is often able to mask her true feelings about dating and relationships, despite her deep longing for connection. She explains, "I’m incredibly good at masking the fact that I’m okay when it comes to wanting to be in a relationship." However, she acknowledges that this behavior has roots in her past, particularly a painful breakup that left her emotionally scarred. Chloe's decision to continue filming despite her emotional state marks a moment of deep authenticity. Rather than sticking to her original plan of sharing a funny dating story, she chooses to embrace vulnerability and be real with her audience. This decision highlights the importance of authenticity in the online space, where many creators, including Chloe, often present only the polished and positive aspects of their lives. 

 

As Chloe delves deeper into her feelings, she begins to unpack the unique challenges that come with dating as a transgender woman. She speaks candidly about the emotional weight of having to disclose her transgender identity to potential partners. "Not only do I have to get this person to fall in love with me, but I also have to then disclose the fact that I'm trans," she explains. This "double whammy" presents a significant barrier to forming meaningful relationships, as Chloe feels that her transgender identity often becomes the focal point, overshadowing other aspects of her personhood. The impact of this constant disclosure is further compounded by the rejection and objectification she experiences in the dating world. Chloe reflects on how many encounters end in disappointment, whether through outright rejection due to her transgender identity or, more frequently, through individuals seeking only casual sex without any desire for a deeper emotional connection. She shares, "What usually happens is that they just want sex but they don’t want to actually get to know me." This painful reality, in which Chloe is often reduced to her body rather than her full self, is both dehumanizing and soul-crushing. 

 

The emotional toll of repeated rejection is evident in Chloe's words, as she admits that it has led her to shut off her desire for love and affection. She says, "I've decided that I'm going to be independent on my own and not ever have to rely on a man again." While she acknowledges that this mindset is both healthy and unhealthy, she admits that it stems from a fear of being hurt again. The idea of opening herself up to someone and being vulnerable, only to face rejection, has become a significant emotional barrier for Chloe. In addition to her fears of romantic rejection, Chloe also discusses the pain of feeling unlovable, a sentiment that many people, transgender or not, can relate to. She reveals, "I feel like I am unlovable, like I am this broken person." This deep-seated belief is tied to her past experiences, including childhood trauma and abandonment issues. Chloe connects this sense of unworthiness to her journey of transitioning, suggesting that being trans adds an extra layer of difficulty in finding love. "When you go on date after date and you get rejected because you're trans... it really takes a toll after a while," she reflects. This emotional weight is something that many transgender individuals face, as societal stigma and prejudices often make it harder for them to form meaningful romantic relationships. 

 

Throughout the video, Chloe explores how her childhood experiences of abandonment have shaped her current perceptions of love and relationships. She shares that, from an early age, she felt like she was not lovable. This feeling of being "misplaced in the world" has stayed with her, influencing her ability to trust others and form lasting connections. Chloe connects these childhood wounds to her current emotional state, explaining that her transition has exacerbated her feelings of isolation and fear of abandonment. The complex interplay of trauma and emotional defense mechanisms becomes clear as Chloe reveals how she has learned to shut off her desire for love as a way to protect herself. "I've been so good at not getting attached because I've detached that part of me somehow," she says. This detachment serves as a survival mechanism, a way to avoid the pain of rejection and loss. However, Chloe admits that this defense mechanism is not without its costs. She expresses a deep longing for the kind of love and intimacy that transcends physical attraction, something that she misses from her past relationships. She says, "What it feels like to be in love... is so much different to what it's like just having sex without those sorts of feelings." 

 

Chloe's internal conflict is a central theme in the video. While she craves love and companionship, she is simultaneously terrified of the vulnerability that comes with it. "I’m really scared that I’m just going to keep going through life without experiencing something," she admits. The fear of loneliness is palpable, but it is overshadowed by her fear of emotional pain. Chloe speaks about the difficulty of balancing the desire for independence with the yearning for a romantic partnership. She says, "I do want to be Miss Independent, but I also would love to be a team with somebody again." This desire for a partnership reflects a deep human need for connection, as Chloe acknowledges that it is a natural part of the human experience to want a mate. Her thoughts on this biological urge to partner up are particularly insightful. Chloe theorizes that humans are hardwired to seek out relationships, not just for procreation but also for emotional fulfillment and companionship. She reflects, "We are biologically made to want to partner up... we’re not meant to be on our own forever." While acknowledging that this desire for connection may vary from person to person, Chloe’s words resonate deeply with anyone who has felt the emotional pain of loneliness. 

 

Chloe also touches on the challenges of navigating online dating, where her feelings of unworthiness are compounded by judgment and rejection. She explains how some individuals on dating platforms will outright reject her, or worse, only seek her for sex, which reinforces her belief that she is not worthy of love. "That just kind of reaffirms that, okay, I am not worthy of this experience," she reflects. This experience is especially difficult in a world where online dating often amplifies superficial judgments and reduces people to mere profiles or bodies, leaving little room for emotional connection or understanding. Additionally, Chloe speaks about her struggles with body image, noting how the weight she has gained during the pandemic has affected her sense of self-worth. She shares a humorous yet poignant observation about how her clothes no longer fit the way they once did. While this comment is lighthearted, it reveals the complexities of body image and self-acceptance, which can be especially challenging for transgender individuals who may already grapple with societal expectations and personal insecurities. 

 

Chloe’s video, though filled with moments of sadness and vulnerability, ultimately carries a message of hope and solidarity. She reassures her audience, particularly other transgender women, that they are not alone in their struggles. "I firmly believe that I’m not the only trans woman who feels like this or has at least experienced feelings like this," she says, reinforcing the idea that these challenges are not unique but shared among many in the transgender community. Chloe’s openness and honesty in sharing her journey highlight the importance of vulnerability in both personal growth and community building. While the video ends on a bittersweet note, Chloe’s willingness to speak her truth provides a sense of comfort to those who may be facing similar challenges. In a world that often prioritizes perfection and happiness, Chloe’s vulnerability stands as a powerful reminder that it’s okay to feel broken, to long for love, and to seek connection - even when the path seems difficult and uncertain.

 

via: youtube

Image credits: YouTube and Instagram

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