Seeing Jean Again, for the First Time

Back when I was desperate in 2010, I used to utilize craigslist and other dating websites to find women to date.  It was a painful time for me.

But one story stands out as something unbelievably unique and comedic.  And it wasn’t until 3 years after the story began that I found out how it was going to end.

I met a girl named Amy online, and after several intimate conversations, we decided to meet.  After spending several weekends socializing, we decided we were better off as friends.

I still continued to visit her at her place, and she had several roommates and friends that would come over and visit when I was there.  The entire group of friends consisted of girls.  Only I was still presenting as male at the time.
So naturally, they all met my former self, and called me by my boy name of ______.
______ became quite the popular fellow, as I knew how to interact with them.  I was sweet, a good listener, and gentle with all of them.  I said the right things and I fit in perfectly with the group.  In a very short period of time, some of Amy’s friends began asking if they could date me if Amy herself wasn’t interested in me.

She gave one friend in particular, Jean, the green light.  “Go ahead, you can date him.  We are just friends.”

Even though Jean and I spent some time hanging out, we never dated, even though I knew she was attracted to me.

Then Amy moved up north to take a job, and most of the group disbanded.   I mainly stayed in touch with Amy, and that’s how things remained for quite some time.


It is now 2013.  Amy visits Los Angeles monthly, and we always make an effort to get together.

Out of our entire group of friends, I had told only Amy about my gender transition.  She promised she would keep it private until I was ready to tell the other people in our old group of friends.

However, her friends always text and call her when Amy and I are hanging out.

Each time Amy was asked who she was hanging out with, she always responded “I was seeing Natalie.”

“Who is Natalie?” her friends would always ask.

“Oh, just a friend from a while back,” Amy would always say.

“Bring her by, we want to meet her!” her friends would say.

I kept delaying meeting up with them because I was hesitant.  Mostly because I didn’t want to come out again, and I didn’t want to have to explain myself.  And because I simply wasn’t ready.

And even though Amy encouraged me to meet our old friends and get it over with, she was nevertheless respectful about my choice in delaying coming out to our old friends.  She was such a good sport for making spare time to see me, when really, it would have made more sense for me just to come out sooner so the entire gang could reunite, and more importantly, so that my old friends could finally meet and see the real me!

But a few weeks ago, something inside me clicked.  I knew I was ready.

Amy was in town for the weekend, and she told me the old gang was going out clubbing in Santa Monica.  I hadn’t gone dancing for a while, and I really wanted to go.  The only way to go with Amy was to meet up with the old gang.

I was cornered.  I chose the harder and more rewarding path.

And what a night it turned out to be!

I got to Santa Monica, to Jean’s sister’s house.  Amy greeted me at the driveway outside, and I was really nervous.  But I was ready.

Then, when we approached the apartment door, I pulled Amy to the side.

“Did you tell anyone about me?” I asked her.

“No, I left it up to you to decide,” Amy said.

“I have an idea,” I said in a giggle.  “I want to see how long I can pass in front of them.  If you work with me and play along, we can have some fun and see if Jean connects the dots and recognizes me.  What do you think?”

“Sure!”  Amy giggled.

I thought for sure Jean would recognize me.  After all, she had spent an enormous amount of time with ______, and surely, she would recognize me the moment she saw me.  I hadn’t undergone any surgeries, and I was still the same height, minus the 4 inch heels I was wearing in preparation for doing damage later that night.   Jean also had a crush on me at one point.  I wasn’t going to pass for longer than 5 minutes, I thought to myself.

I remember being so nervous as I entered the apartment.

“Everyone, this is Natalie!  Say hi to her!” Amy said.

“Hi!!!  So nice to finally meet you!  I heard great things about you,” said Jean’s sister Jel.

Jean had her back turned to me, as she was still getting ready.

She turned around.

My heart stopped.

“Hi!  Nice to meet you!  Amy has mentioned you so many times, nice to meet you finally!” Jean said.

She didn’t miss a beat as she continued changing outfits and getting ready.  There were a total of 6 girls that night, and the apartment looked like it had thrown up clothes all over the floor.  I felt like I fit right in, and was totally in my element.

And Jean didn’t seem to recognize me at all.

So how do you know Amy?” Jean asked me.

“We met through some mutual friends,” I said.

We talked to each other for the remainder of the night, and she asked me all sorts of questions, such as what I did for a living, what ethnicity I was, and where I lived.  I thought for sure those things would give me away, as I was still of Chinese American descent, still an engineer, and still living in the same city.

She didn’t put 2 and 2 together.

I looked at Amy several times as the other girls were gathered in the bathroom, and we both giggled.
It was our little secret for the night, and my evil little plan was working.  I was having a blast with my strategy of the night, and it was being played out to perfection.

Now don’t get me wrong.  I believe there is much power in owning our transgender history, and there is no doubt about where I stand with the topic of passing.

But this was so much fun.  I just had to see it through, as I was having way too much fun witnessing the binary rigidity in people’s thinking play out right in front of me.  Besides, I was eventually going to tell them.  I just wanted to see how far I could take this theme, and I also wanted to know how much I really passed in front of people, even if they had seen the old me before.

I got my answer.

For the rest of the night, we danced until 2 AM.  I got hit on by several guys, and one in particular kept talking with me, and ended our conversation with: “I know you probably get this all the time, but I just have to say you are very sexy and beautiful.”  It was an all around amazing girl’s night out.  I even danced with Jean and she cheered me on, without anyone being the wiser.  Amy kept giving me little smirks and smiles, and we knew our secret was safe.  It was too funny.

At one point, she even texted me “I don’t think she knows!”

We got Jack in the Box and headed back to Jel’s apartment, and we hung out until 3 AM.  It was wonderful.  I was so happy and so in my element.

Then Jean said, “Hey Natalie, before you go, let’s exchange numbers so we can hang out again sometime!”

I agreed, but then quickly realized that my number has been the same for the past 10 years…and that if she didn’t delete _____’s old number, then upon putting in my number, my old name would pop up in her screen.

“Uh, why don’t you give me YOUR number INSTEAD?”  I said.

She did, and I quickly put it in my phone and told her I’d text her on my way home.

On my way home, I said to myself out loud: “What a night!  Can you believe it?  You GO NATALIE!  Work it girl!!!”

Not a clue!!!

It was great seeing each other again, both of us for the first time.


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