‘This would kill her.’ She was 96, and if she passed from anything coinciding with my coming out, I’d be blamed.’: Trans woman shares long-awaited coming out journey

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“We all make changes in our lives. Some out of dreams we’ve had for a long time. Others out of necessity. I made a huge change at 45, and it was one that encompassed both of these reasons. But I’m not going to tell you what that change was just yet. Interested? Read on.

Growing up in a small town in Indiana in a Fundamental Evangelical Baptist family had its frustrations and rewards. My parents loved one another. They loved my older brother and myself. With this love, however, came things you just knew you didn’t talk about. This was ingrained in me through our church (three times a week) but then compounded when I started attending their school. I was basically told what a horrible person I was, and they didn’t even know what was happening inside me. To them, it was just a blanket teaching that covered all things homosexual. That wasn’t even exactly it, but they made sure to encapsulate everything under that blanket of hatred. We were taught this every day, and that was on top of the church sessions. Saturdays were my respite. I’d ride my bike into the country and let out the frustrations. I would scream, cry, dance, lie down…really, anything I could do to forget the previous week and make myself ready for the battle to start up again the next day.

woman when she was in kindergarten
Courtesy of Jen Winslow

OK. I’m trans. I was going to hold off and let you all figure it out as I went, but there it is. I kept that secret for a lot less time on the page than I did in real life. In life, I made sure to never draw attention to myself. I did not need any scrutiny, so I walked the line. I was smart but made sure I never excelled at anything. I wasn’t as masculine as my classmates, but I was careful not to be feminine. My 6th-grade teacher kept me after class when she returned from maternity leave. The reason? My handwriting. She was concerned it was too ‘loopy.’ Her exact words were, ‘I was afraid this was going to happen.’ My writing was too pretty, and boys didn’t have pretty writing. She gave me a hug and said life wouldn’t be kind to me if I kept this path. She knew it was more than the handwriting, but that was the end of the conversation. So, I altered my writing style to once again fit in. It wasn’t a huge deal, but, again, I needed to stay hidden, so I went with that.

I had a timeline. Graduate high school, move to California, transition. That wasn’t going to work out because I had no money, so I altered it a bit. Graduate from college and then move. By my mid-twenties, I’d be on the West Coast living as who I knew I needed to be. But…college. Things happen in college. The thing that happened to me was I fell in love. I honestly never thought it would happen to me. I was always focused on other things. I guess that’s when it happens most often.

person graduates from high school
Courtesy of Jen Winslow

It was a wonderful relationship. The one thing I insisted on was being truthful right at the very start. We discussed how I felt. When this might happen. IF it would happen. Then something else happened. We were going to have a child. We got married with a year left in college for me. All my plans were now on hold. I had a family, and that had to come first. My dreams were put on hold for a few years. Well, twenty-two to be exact. The marriage was great. We loved each other. We had open communication with one another, but the quest of transitioning really took a back seat to everything. The years passed and the talk of transitioning came back. It was strong, and I needed to let my wife know. So, we talked at great length about it. It was still theoretical, and she said we’d stay together no matter what. Then the night came that changed the conversation to reality.

We were out to dinner. I was presenting as Jen. My wife grabbed my hands and asked, ‘Are you happier as Jen?’ I didn’t answer. She squeezed my hands and looked deep into my eyes. ‘It’s OK,’ she said. ‘You can tell me. I love you.’ My reply came as a whisper: ‘Yes.’ The next day we began the search for what needed to happen. What the next steps were. This took a little time as I didn’t even know where to begin. I became Jen 95% of the time. The only time I wasn’t was at work or around my parents. It was during this time that my wife said she couldn’t do it any longer. As I was becoming more feminine, she was less attracted to me. The love was still there, but the physical attraction was not. We were going to divorce.

During that time in limbo, I began coming out to friends. Social Media made this an easier task than in the past. I came out to a few close friends, who I knew would be accepting and supportive. Then I released a blanket invitation to friends to come to the new page. Now, I must admit I had been giving lead-ins prior to this announcement. Some thought divorce, others thought I was being arrested for something…let’s just say that vague is not always best. But once the new profile was up, friends flocked to it. I received emails, phone calls, DMs… all congratulating me and showing support. It was beautiful. Then came the hard part. I had to come out to my parents.

trans woman with partner before coming out
Courtesy of Jen Winslow

My parents are snowbirds, meaning they go to Florida for the winter months. It was 2012, the year of their 50th anniversary. I didn’t want to come out prior to that and mess everything up for their big day, so that left the first three weeks in October to tell them. I had been helping my dad learn how to edit videos on Saturdays, and I finally said, ‘Next week, I have something very important to tell you. You can’t let me leave without sitting you both down.’ He agreed. Knowing I could not get through it off-the-cuff; I wrote it out as a letter to them. A letter I would read, or at least reference, as I came out.

The next Saturday arrived, and the time came. I had them sit in the family room, and I began. I spelled it all out for them in the form of a chronological experience. I described how I used to color my fingernails with crayons and then scrape it off before they came home. When I was done, my mom was full of guilt. The ‘what did I do wrong?’ kinds of questions. My dad got it more quickly. He told mom that she did nothing wrong, this was ‘…just the way God made her.’ (Can I just let you know the impact of that statement? Correct pronouns!) As I said goodbye for the day, I got the first two-armed hug I’d received from my dad. He wouldn’t let go. He was in tears. He was happy. He knew I’d been hurting. He pledged the support of the entire Winslow family, saying they’d either get it or have to answer to him.

Aunts and uncles chimed in with their concerns. Did I know what I was doing? Is this a phase? A phase!!??  I was 46 years old!!! Whether they got it or not, they all shut up about it. What I was told, from those well-meaning relatives, was to never tell my Great Aunt Grace. Why? ‘Because this would kill her.’ Now that is quite the guilt trip to hang over someone. She was 96. At that age, she could pass from anything that might coincide with my telling her, but I’d be blamed. So, I didn’t tell her. Well, I didn’t tell her for two years. I sat with this request from relatives and my own relationship with this remarkable woman. I knew she’d be OK with this. I knew she’d understand. I mean, I used to look through telescopes with her, and we’d discuss life outside of earth. She fully believed in other life in the cosmos. So, I told my parents to let everyone know I was telling her. I was coming out!

trans woman wearing overalls, feeling comfort in gender identity
Courtesy of Jen Winslow

I wrote a letter from the heart to explain everything to her. No edits, just free-flowing emotions. I even included a page of photos with me and my new trans siblings. I held my breath as I mailed it. Was I making a mistake? Too late now.

A few weeks went by. No response. My parents said that she got it and was replying. They also said she loved my writing style and said I really needed to become a writer. She said this repeatedly, I was told. Then the day came. A handwritten response in the most perfect cursive. She began by catching me up on her and then immediately responded with acceptance and love. She said her late husband had spoken with several trans women during his time as a Unitarian pastor. He embraced all of them, as did she. She mentioned that Caitlyn Jenner’s coming out helped with filling in blanks as well. She thanked me for introducing her to Jen and could not wait to meet her in person.

As a family, we all planned to gather for her 100th birthday in 2018. Sadly, this did not get to happen. Just shy of her 99th birthday, she passed away. Her heart slowly going throughout that fateful day. She just felt tired and fell asleep in the hospital. That was the end. I was not blamed for this, and I am eternally grateful that I came out to her. Grateful that she got to know Jen, even briefly, and to see photos of my new life. Nothing had changed between us. We still held deep conversations, through letters and emails, about life and all the wonders it held for us.

trans woman wearing a pink shirt and ripped jeans
Courtesy of Jen Winslow

My life changed a bit after coming out in general. I was happier than I’d ever been. I opened up creativity that I’d buried away for decades. In 2013, I began hormones on February 18, celebrated our 22nd anniversary on the 23rd, filed for divorce on the 28th, and was officially divorced on April 1 (how appropriate). In May, I heard about a job in California and applied. I got hired! On July 4, I left everything I had ever known for 47 years to start completely over.

I’m 55. Not the same 55 that my parents were. I have a wonderful chosen family of trans and cis siblings. I perform standup comedy, I write (you were so correct, Aunt Grace), and I act. The process of figuring out oneself is enlightening and terrifying. By the time I had found a therapist, he thought I’d already transitioned. He congratulated me on what I’d discovered and processed on my own. It was tough. There were no other trans folk in my area. Now, after these past 8 years, there is a thriving trans community, and Muncie, Indiana just had its first Pride in 2020.”

woman living a happy life after coming out
Courtesy of Jen Winslow
woman with a mic, happy and proud
Courtesy of Jen Winslow

This story was submitted to Love What Matters by Jen Winslow. Submit your own story here, and be sure to subscribeto our free email newsletter for our best stories, and YouTube for our best videos.

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‘We don’t want to hear you’re ‘sorry’ for us. We don’t want to ‘fix’ her. We thought being gay was sinful. Let us be clear: WE WERE WRONG.’: Family ‘honored’ gay daughter came out of the closet

‘Are you a boy or a girl?’ My daughter responded with the craziest look on her face. ‘I’m a girl!’ I knew she was gay. I always knew she was ‘different.’

‘Just give her time. She’ll come around.’ My mom has yet to use my correct pronouns. To her, I’ll always be her first ‘daughter.’: Trans man finds courage to live his truth, ‘Transitioning was the biggest act of self-love’

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