Growing up in Summerland, British Columbia, amidst the family winery, Sumac Ridge, Dee McWatters was immersed in a world where wine was more than a drink, it was culture, ritual, and connection. Though neither she nor her sister initially planned to pursue careers in the wine industry, Dee’s path seemed almost destined to intertwine with her family’s legacy, blending heritage with her own passions and creativity. These experiences, paired with a family environment that embraced discovery and expression, laid the groundwork for a life lived fully, without fear of breaking molds. Dee’s journey of self-discovery took on profound depth when she began her transition. Her memoir, Sorry I Was Such a D!ck, When I Had One!, is at once funny, honest, and deeply personal, capturing the moments of reflection, struggle, and catharsis that accompanied her transformation. Through writing, Dee confronted emotions long suppressed, finding both liberation and self-realization. Transitioning publicly in her forties, she navigated societal expectations, internalized pressures, and the challenge of redefining herself while remaining true to the values she had always held.
But Dee’s story is not just about personal transformation, it is about advocacy, community, and lifting others as she rises. From her early days as a firefighter, hockey official, and business professional, she learned the importance of fairness, safety, and inclusion. These experiences shaped her approach to equity, diversity, and inclusion initiatives, allowing her to champion underrepresented voices, break down barriers, and educate communities about meaningful allyship. Her commitment to creating spaces where everyone belongs reflects her belief that kindness, courage, and action are inseparable from a life well-lived. Today, Dee dreams boldly, striving to make global impact while staying rooted in local community. From speaking engagements and EDI consulting to considering a run for town council, she continues to inspire through action, showing that living authentically and using one’s voice for change can coexist beautifully. Dee’s life is a celebration of courage, joy, and transformation, a reminder that our truest selves are worth embracing, and that by standing in our authenticity, we create space for others to do the same.
|
| "The truth was I had never considered myself a writer." |
Dee: Being immersed in the wine industry from an early age was a unique experience for a Canadian kid. It was very new, and my family had a more “European” attitude towards wine and drinking. It was part of a meal, meant to be enjoyed in moderation.
Both my sister and I had different aspirations for our careers while growing up, and neither of us initially wanted to be in the wine industry. As we reached our late teens and early twenties, we realized it was what we truly enjoyed and knew, and it ultimately felt almost destined to be a part of our lives.
Monika: If you had to pair your life story with a wine, would it be a bold Cabernet, a complex Merlot, or a sparkling wine that surprises everyone at the first sip?
Dee: Well, in the late 1980s we introduced Western Canada to the first traditional sparkling method wine produced in the region, and as a result, we began consuming much more sparkling wine. My dad used to say, “If it doesn’t go with sparkling, then don’t put it in your mouth!” We quickly realized how versatile sparkling wine and champagne are, it’s not just for celebrations. Bubbly is perhaps the most well-rounded wine, to be enjoyed however and whenever. It is vibrant, fresh, friendly, lively, and appealing to the masses.
Monika: Your memoir, Sorry I Was Such a D!ck, When I Had One! (2025), is funny, honest, and deeply personal. What motivated you to write it, and what did you hope readers would take away?
Dee: About a year into my transition, I began reflecting on all the moments growing up, through adulthood and parenthood, asking myself if I knew I was transgender or what little hints I should have noticed. I decided to take notes and journal all these feelings to try to understand my own journey and path. I shared some early writing with a good friend, and after a weekend she said, “I never knew you were a writer. Why didn’t you ever mention this?” The truth was I had never considered myself a writer, I hadn’t written an essay in over 20 years. She encouraged me to shift from journaling to imagining I was telling my story to another person. That’s how I decided to write for an audience larger than just myself.
Monika: Were there moments while writing it that surprised you about yourself?
Dee: The process of writing was very cathartic. As I remembered suppressed experiences, I confronted many emotions I had not dealt with. It wasn’t easy, sometimes writing plunged me into deep depression. However, there were also moments of discovery, joy, and self-realization. Every time I wrote and revised, I experienced those emotions again. As challenging as that was, it allowed me to find some inner peace.
|
| "The process of writing was very cathartic." |
Dee: Moving from the Vancouver area wasn’t a big change for me. I was born in a Vancouver suburb, but we moved before I was five and before I started school. My friend circle was limited to neighborhood kids, and I hadn’t experienced living in a large city despite being close to one. I have always been a small-town person; however, with connections to a larger center and family still nearby, visiting the city never felt foreign to me either.
Monika: Aside from working in the winery, what childhood hobbies or passions left a lasting impression on you?
Dee: I grew up with sports. I loved participating, especially ice hockey. I started skating at the age of 3 or 4, began playing hockey at 8, and officiating at 12. To this day, at age 51, I still play and officiate, and in fact, I do both more than ever. Around the age of 10, I took up running, and through high school I was on the cross-country and track teams.
At 18, I ran my first marathon, and at 22, my first Ironman Triathlon. Today, I still swim, bike, run, and now mountain bike, cross-country ski, downhill ski, and hike. I’ve always loved the rush of endorphins from exercise. It has been a wonderful way to manage stress and depression.
Monika: Do you think marriage was ever a way of running from yourself, trying to quiet inner doubts by choosing a life that felt safer or more expected?
Dee: Marriage was never a way of running from myself. I always dreamed of getting married, having a family, and being an involved parent. Looking back, perhaps it felt like “just what you did,” but I never saw it as hiding. I didn’t question romantic attraction or necessarily question gender identity, beyond some thoughts about gender expression. In the late 1990s, being from a small town, I simply hadn’t been exposed to the diversity of people and genders that exist today.
Monika: How has your relationship with your former spouse evolved throughout your transition?
Dee: My former spouse and I separated in 2010, and I did not come out until 2018, so my transition was not the cause of the marital breakdown. For many years, our relationship was simply that of co-parents, and it was fairly chilly. Once I came out and began my transition, I feel my former spouse became less angry about the breakdown and the relationships that followed. Today, we are cordial, maintaining a respectful connection.
Monika: Choosing a name is such a deeply personal decision, one that can hold layers of significance and meaning. How did you come to choose the name Dee? Does it carry a special resonance for you, perhaps representing a part of your journey or embodying a particular feeling or aspiration?
Dee: Early in my days of self-discovery, I wouldn’t even have called it transitioning, as I was still deeply in the closet, though my sister knew. I wanted a name that was more feminine, or at least gender-neutral, that I connected with. I tried names like Danielle and Delilah, but I wanted one starting with D, as my name was Darren. One afternoon, my sister suggested that, until I decided, I could simply be referred to as “D” by those in my close circle.
Several months later, my new name literally stared me in the face. At my local bank, a teller’s name tag read “Darrian,” and it hit me, so obvious! By adding an “i” to my existing name, it became Darrien, with the “i” standing for “identity.” “Dee” became my everyday nickname, while Darrien remains my legal name. Sometimes it’s a little confusing, but it feels right.
|
| "My mother was the last of my immediate family I came out to." |
Monika: Do you remember the first time you met a transgender woman in person? What was that experience like, and how did it make you feel?
Dee: The memories are a bit faded, but I believe I was at a gay club in California. I was curious and ended up dancing with a couple of women. At the time, I didn’t know if they were drag queens, cross-dressers, or trans women. I was nervous being alone in a gay club and had no idea what I was seeking. This was about eight years before I truly understood who I was.
Monika: When you came out, did your mother embrace you as her daughter? And do you feel any connection to her in the way you look, carry yourself, or even in your style and mannerisms?
Monika: When you came out, did your mother embrace you as her daughter? And do you feel any connection to her in the way you look, carry yourself, or even in your style and mannerisms?
Dee: LOL! No, it wasn’t instant. My mother was the last of my immediate family I came out to, not because I doubted her support, but because she doesn’t adapt to change quickly. It took her time to adjust to new names, pronouns, and my expression of self. That said, she is supportive. I do see some similarities to my mother in my appearance, though my sister and I have a good mix of both our parents. My sister and I, in particular, share some striking similarities.
Monika: Many of us feel the pressure to “pass” as women, and even after surgeries, society keeps judging us. How do you personally deal with the outside world’s expectations?
Dee: Yes, it was a struggle. I wanted to “pass” so much, but not necessarily for others, it was about my internalized expectations of how I should look. I started transitioning publicly shortly before my 44th birthday, and in the first couple of years, I desperately wanted to look and feel like a 20-year-old woman. The challenge was, of course, that I was 44-45, pre-HRT.
Over the years, my expectations shifted. Now it’s about feeling feminine as a 52-year-old woman, but with the style of a 32-year-old. I’ve always loved fashion and makeup, not to “pass,” but because it reflects how I feel and express my femininity. Most people are often shocked to learn my age; I’ve even been mistaken for 10 years younger.
|
| "I do like compliments." |
Dee: Regarding gender, there’s no question, I am a woman, whether dressed up for a night out, in sweats and a hoodie, after a hockey game, or on the beach in a bikini. I try to show that there is no single way to be a transgender woman, a woman, or a human. Have I had surgeries? That’s private. Have I had GRS? Yes, one surgery, and it was solely for me, to feel complete as the woman I’ve always been inside.
Monika: I remember the time right after my transition, it was pure euphoria. My closet is still full of dresses and shoes that I literally bought by the dozens back then, and I must have tried on hundreds. I felt like I had to make up for all those years that were taken from me. Did you feel the same way?
Dee: Yes, there were definitely moments like that. Pre-transition, there were binge and purge cycles, but once I started transitioning, it became more about: Who is Dee? How does she present herself? What is her style and expression? I actually had help from my good friend’s 15-year-old daughter! LOL.
Monika: How has your style evolved since then, especially as your life and career have changed?
Dee: My style has evolved over the years. I’m still figuring out what’s in, what’s out, and most importantly, what I feel comfortable in. In the past two years, I’ve discovered my “brand.” As a self-employed consultant and professional speaker, my style now includes stylish, colorful blazers, pink, purple, and always a medium-brimmed hat! I still wear jeans with polo or golf shirts, and hoodies, but for business and presentations, flowy dress pants, blazers, and a compliment of hats are my go-to.
Monika: Do you love playing around with makeup, or is it more of a “throw on the basics and go” kind of vibe for you?
Dee: Daily, it’s usually the basics: foundation, eyeliner, and mascara. But I do have a decent stash. I can contour, and eyeshadow is never just one color! When I do my eyes, there’s usually layering with about three colors. I have some amazing friends who taught me well, so I’ve learned a lot along the way.
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or do you struggle with believing them?
Dee: I do like compliments. I used to feel awkward, as if people were just being nice, but I realized how genuine they were, especially from my cis female friends. Compliments like “You’re killing it, girl,” “Damn, your makeup is fantastic! I don’t think I could have the patience,” or “Could you tell me your secret?” feel amazing! The compliments are genuine and uplifting.
|
| "I love friendships and social connection." |
Dee: I did feel that pressure, but only the pressure I put on myself. I’ve always been my own toughest critic. I felt I needed to look, walk, talk, and apply makeup like the “ideal” woman. But what is the ideal woman? There’s no true answer.
One who likes herself, has confidence, and is happy with who she is. There’s no pressure anymore. Media portrays unattainable ideals, and in a strange, affirming way, I was experiencing what most adolescent girls feel, chasing an impossible ideal! LOL. And then I grew up… somewhat.
Monika: What was the most surprising part of your transition, something you never expected, whether good or bad?
Dee: Two things stand out. One, which wasn’t so great but still affirming as a female, was recognizing overt and covert misogyny toward women. I’ve been treated differently, questioned about my experience and expertise, things unrelated to gender, like my knowledge of hockey, ability to drive a forklift, or backing up a truck and trailer. Duh, no shit, I’m a good driver! Gender has nothing to do with it.
The second, overwhelmingly positive surprise, is the number of women I’ve become friends with. Most of my friends are cisgender women, who have been incredibly supportive. Friends from high school, casual acquaintances, and even long-time male friends have grown even closer after my transition.
Monika: For a lot of trans girls, loneliness can become a part of life. Did you ever feel that, or were you lucky enough to avoid it?
Dee: For the most part, I’ve been able to avoid loneliness. Early in my transition, I didn’t have many transgender friends and didn’t actively seek new ones. My workplace was predominantly female, 75% of employees and management, and from 2018 to 2024, everyone only knew me as Dee. This made the transition easier. I make friends easily because I’m an extreme extrovert! I love friendships and social connection. That said, when the pandemic hit, the first few months of isolation were awful, and I nearly committed suicide.
END OF PART 1
All photos: courtesy of Dee McWatters.
© 2026 - Monika Kowalska
No comments:
Post a Comment