I am often asked “When did you know you were transgender?” or some variation of that question. And while some trans folks can say they’ve always known, that’s not true for me. I had these series of ah-ha moments throughout my life that I call my lost boy memories. They’re brief moments that at the time made me aware that I was different, but in a way I couldn’t put into words yet. Looking back now, it’s clear these were moments that the little lost boy inside was trying to find his way out. This week I will share three of those memories that make up the many pieces of my journey towards coming out and living my truth.

Lost Boy Memory #1

I was five-years-old, walking with my dad along a California coast when I paused and looked up at him and exclaimed; “I want to be a boy.” My dad replied without hesitation, “Ok. Why do you want to be a boy?”  I explained, “I want to play basketball like other boys and marry a wife when I grow up.” Again, without hesitation my dad replied calmly and matter of fact, “You can play basketball and have a wife AND be a girl.” And with that we continued walking. At five, this answer solved my immediate conflict, for the moment. This would be one of many moments over the next 25 years that my little lost boy would try to find his way out of my female assigned body.

Lost Boy Memory #2

We visited my paternal grandparents twice a year; once around the holidays and once during the summer. Both visits inspired clothes shopping trips with Grandma, which consequently caused tension to rise between my dear Grandma and me. Grandma really wanted me to have nice dress clothes, and since I was her only granddaughter this meant super frilly and lacy pink and purple dresses. And I really wanted baggy jeans, batman tees and light up sneakers. My dad would play mediator, preventing a department store war from blowing up. He would show my grandma and me androgynous clothes compromises that we could both agree on.
There’s one year in particular that I remember. I was 10, and the dreaded shopping outing happened. I found these plaid slacks that had suspenders attached to them that I “HAD TO HAVE!” I strutted proudly up and down the dressing room, trying to sell my grandma on them. She agreed, and even let me get a pleather jacket to go with it. When my brother and I got back to their house I quickly changed into the new outfit so I could model them for Grandpa. I remember feeling so confident in my slacks and suspenders, I felt good and I knew I looked good.

Lost Boy Memory #3

I was probably about 12 or 13. I was visiting my dad for the summer in California. We went to get me a wetsuit so I could boogie board in the ocean. The only one that fit me in our price range (wetsuits are ridiculously expensive, FYI) was a used red and black boy’s wetsuit. I remember my dad asking if I was ok with wearing a boy’s wetsuit.  And I remember being ecstatic to have a boy’s wetsuit.

Later that weekend we went to the beach and I was boogie boarding to my heart’s content.  My hair was short and the wetsuit took away all the small curves that had started to appear on my body. As I had finished riding a wave in and was about to go back out a girl approached me. She twirled her hair with her finger and in a flirty tone asked “Is boogie boarding hard?” I smiled and said “No. It’s pretty easy, unless you catch a rough wave.” (I didn’t want her to think it required zero skill.) She asked me if I would show her how. And I said I would. I had realized from the very beginning of her approach, that she was flirting with me, and that she thought I was a boy. I also was aware that I liked that and that I wanted her to continue to see me as a boy. It was then that my luck ran out, my dad called from shore “JENNY! It’s time to go!” And without thinking I automatically responded and then looked back panic-struck at the girl, in my head praying “Please let her have heard Jimmy, oh please, oh please let the wind have distorted it and she heard Jimmy or Jennings or anything but Jenny.” She had definitely heard Jenny and she definitely connected the dots and realized that made me a biological female, and with that she ran away faster than I thought possible.

I grabbed my board and moped back to the beach, where my towel was. I didn’t know why yet, but I was really embarrassed that my cover as a boy had been blown. Later I would realize that this was yet another time the little lost boy inside me was trying to find his way out.

Previous Post: The Best Pick-Up Line Ever

Next Post: Dating While Trans