I never had bad luck with dates or flings, especially with the kinds of men who look good on paper. There was the corporate lawyer. The investment banker. The diplomat. The doctor. The congressional aide. Even when I was out traveling for work, I often had drinks or dinner plans with a guy.
Yet my trysts with these men never led to anything meaningful. There were similar interests, physical chemistry and a mutual desire to see each other again, But I often never got past the first few dates because of my gender identity. These successful, desirable bachelors on top of the world were terrified to go any further with a transgender woman like me. They were fearful of anyone questioning their masculinity. They were also shaken by the thought of anyone doubting their sexual orientation as anything but straight.
On one occasion a guy was driving me back home after a fun and romantic night of wine, a few rounds of Jenga and good conversation. I considered the evening nothing but a homerun, but any hopes of a second date quickly vanished when we arrived at my place.
"Can you do me a favor?" he asked while slowly pulling into the driveway.
In my dating experience, catchphrases like that at the end of a date usually meant one thing: Don't expect much. I wanted to hope he was going to ask me something completely different from what I had become accustomed to.
"Sure," I replied evenly as my heart began to sink. "What's up?"
"Do you mind if we keep tonight between us?" He nervously glanced over at me, perhaps already aware that I'd known what he was going to say. "I'm not sure who we may know in common, but I don't want people finding out."
A brief silence filled the dark car.
"That shouldn't be a problem," I responded with a steely smile. I unbuckled my seatbelt, opened the door and got out of the car. I turned back to look at my date, who avoided making eye contact. "Good night."
I proudly marched toward the house with my head held high, but the bitterness, humiliation and tears burst forward when I was back in the safe confines of my home.
It didn't matter that I came from a good family and had a solid group of friends, that I had a successful career or that I possessed a wide range of interests, aspirations and quirks. Even on a superficial level it didn't matter if I possessed a killer set of legs. I was constantly being pushed away or kept out of sight by men attracted to me but terrified of what everyone else might think of dating a transgender woman.
The same question would run through my head after I recovered from these kinds of bogus dates: Why wasn't I ever enough?
And how can transgender women like me feel like we're enough for someone else when a majority of us live in dire circumstances? Many transgender women face abysmal access to education, health care, employment and housing. We face constant scrutiny by the world around us, and frequently that scrutiny begets violence.
The vicious cycle of guys treating me like their dirty little secret was always on repeat.
Meeting that special someone seemed so out of reach as opposed to the immediate gratification of a one-night stand or passionate fling. I wanted to find the person who was not only attracted to me but was proud to be with me because I was their find of a lifetime.
Nowadays most young single professionals turn to the Internet for meeting someone. I was no exception. For me, online dating was somewhat ideal for meeting like-minded people. And it was also a safer bet to be open and upfront about my gender identity before agreeing to meet someone and getting my hopes up.
That's how I met Drew. At first we exchanged simple but friendly messages, allowing both of us to get to know each other. I learned that Drew had fulfilled a life-long dream in his recent move to the city. He liked to cook and surf and had an eclectic taste in music. In the process I was surprised to discover that he was a Korean adoptee.
I told him about living in the city for almost over a decade. I talked about working for a national LGBT organization. I shared that I too was a Korean adoptee, having found my family in Korea only a few years ago. I also reiterated that I was transgender and in the midst of my transition. I wanted to make sure he had paid attention to everything that I'd originally written about myself.
I found Drew's response to be unexpected and rare: "That's awesome! Identity is always something to be cherished." Toward the end of his message, he wrote, "Would you be up for dinner? I'd like to get to know you better."
I quickly turned away from my laptop, somewhat hesitant to reply. I could feel my dating insecurities begin to bubble up. I cringed at the idea of yet another guy asking for our time together to be kept a secret, among a series of other degrading requests. I didn't have the appetite to deal with any more men with deep-seated fears of dating me.
But I also began to wonder if this date could somehow be different. I swung my chair back around to face the glowing screen. I began to reread Drew's messages from earlier, messages filled with kindness, plentiful jokes and a strong interest in knowing more about me.
I bit my lip, pondering this dilemma. I wanted to gradually let down my guard. I wanted to become vulnerable with someone who could start to mean something to me. But that meant I would have to take a risk.
I sighed and replied yes.
On a cold New Year's Day I found myself meeting Drew for dinner at one of the many restaurants in Manhattan's Korea Town. He was waiting outside, and a smile instantly formed on his face when he spotted me in the bustling crowd.
"Hi," I shyly said as my cheeks begin to tingle. I couldn't help but admire how handsome he looked. He wore a well-fitted wool overcoat. Underneath I could make out a sweater that complemented his slacks and brown Oxfords.
Still smiling, Drew motioned toward the restaurant entrance. "Let's go inside and warm up."
Drew held the door open for me, and we were immediately greeted by the enticing smells of Korean barbecue and spicy soups. An elderly but no-nonsense woman guided us to an empty table amidst the hectic traffic of servers zipping in and out of the kitchen. We exchanged furtive glances over the tops of our worn menus and then smiled. Both of us were nervous, but in the best way possible.
All my earlier hesitations quickly dissolved into the steaming dishes that were brought to us. We swapped stories and laughter over dishes of spicy pork, bubbling stews and the endless amount of side dishes on our table. Much later we found ourselves at a nearby diner sharing dessert as we continued talking about anything and everything that came to mind.
It was past midnight when our date came to an end. We both walked to the same station, taking the train in opposite directions.
As we finished saying our goodbyes, he leaned in and gently kissed me. "Get home safely. I'll talk to you tomorrow."
I touched my mouth and looked back at him speechless. He met the surprised look on my face with a big grin and waved as he descended the stairs to catch his train.
That night I could feel the butterflies flutter in my chest. Something was different this time around, and it was Drew. Already he stood apart from all the others.
Our time together always taught us something new about each other. Drew schooled me in how to play a mean hand of poker. I taught him how to make fresh Korean dumplings and kimchi. And it became clearer with each date that we were falling for each other, hook, line and sinker.
It was on Valentine's Day that the depth of our feelings for each other was confirmed. After a memorable five-course meal, Drew took me home and presented me with a card and gift. I sat cross-legged on my bed as I used my finger to carefully open the sealed envelope.
Then I noticed how he'd signed the card: "Love, Drew."
I slowly looked up at Drew, who was already staring at me with a nervous, lopsided smile. It was clear that he was putting on a brave front for what I was about to ask him next.
"Did you mean every word in this card?"
He leaned over and placed my hands into his own. "I meant every word. I love you, Andy."
In that moment I realized that my life was starting to mirror many of my hopes that often went unsaid. Before Drew I was too afraid to allow myself the indulgence of dreaming about a guy loving me as much as I loved him. I long carried the belief that no guy could see me as a woman to love because of my gender history.
I hastily pushed aside the unwrapped gift and inched closer to Drew. I looked over at the card and made a decision. It was time to begin letting go of my shame and charting a new course. I swallowed thickly, choking back tears, and shakily replied, "I love you too."
Drew became the guy who would pick me up from a long day at the office. He was the kind of person who would spend hours perfecting a mixed CD to accompany me on a work trip. The one who would surprise me with flowers. The guy who eventually moved in.
He also became my rock as I continued my transition.
We were relaxing in bed one night when I made an announcement. I put down my iPad and looked over at Drew. "I met with my doctor," I shared, smoothing out the bed covers. "I'm going to start taking hormones."
I was uncertain of his reaction, especially since we hadn't discussed all the details of what the rest of my transition might entail. I was in uncharted territory and braced myself for his response.
Drew laid down his surfing magazine and smiled. "I think you're beautiful," he said without missing a beat. "I have ever since we first met, and I want to be with you no matter what."
I had never considered the thought of being in a relationship with someone when I had yet to fully transition. But I had never anticipated being with someone who would be at my side throughout the process. I buried myself in his chest and felt the tears of relief roll down my face.
Soon thereafter, Drew took me to the doctor's office to pick up my first prescription for hormones and surprised me with dinner to celebrate. He also began to show his support by driving me to the doctor's office for periodic checkups, patiently waiting in the reception area. Even at home he would gently remind me to take my hormones before going to bed. I had not only a boyfriend but a critical ally in my transition.
Our relationship deepened even further as the weeks and months passed by. Soon my birthday arrived, and Drew decided to take me away for the weekend. It would be our first trip together.
We were driving back to the city when Drew announced that we would be passing by his hometown. He looked over from the driver's seat. "Mind if we grab a bite to eat in the area?"
"Sounds good to me." I was hungry, but I was far more curious to see the town where he grew up.
Drew was fairly quiet as we ate at a popular local restaurant. I assumed he would be excited to be home in familiar surroundings, but he appeared distant and pensive. I took a sip of my drink and asked him what was wrong.
"I have a question for you," he shared, wiping his hands with a napkin.
"What is it?"
He took a deep breath and looked directly at me. "Can I introduce you to my family?"
Ever since we met, Drew spoke often of his family and how important they were to him. Early in our relationship he proudly shared that his family knew all about us. Later I was surprised to learn that his mother had even bought a book to learn more about transgender issues after he shared more details about my gender identity.
Never before had a guy told his family about being in a relationship with me, let alone in such an open manner. I was instead used to being treated like a scandalous secret by guys afraid of openly dating a transgender woman. Now my boyfriend wanted to bring me back to his home.
I nervously took another sip of my soda and cleared my throat. "I'm ready if you are."
I frantically touched up my makeup and brushed my hair as Drew drove deeper into the suburban sprawl toward his family's house. I was far more nervous about meeting his parents and siblings than I'd been about some other critical events in my life: submitting my first piece of writing to a national magazine, speaking to thousands of people in Times Square, or even accepting an invitation from the White House to be recognized for my work. I just wanted to make a good first impression.
"Promise to stay by my side?" I asked.
He nodded. "Promise."
We finally parked the car and walked up to the friendly-looking house holding hands. Drew offered me another reassuring smile and gave my hand a squeeze. "They're going to love you."
"Here goes nothing." I nodded my head and took a deep breath as he opened the door.
Drew led me inside to be welcomed by a home filled with years' worth of memories. Family and childhood photos lovingly adorned the walls. Artwork and aced school tests were proudly displayed on the fridge. It was clear that Drew came from nothing but a loving family.
His parents rushed over to greet us, visibly excited by our unexpected visit.
"This is Andy." Drew smiled confidently as he added, "She's my girlfriend."
I smiled, politely extending my hand. "It's nice to meet you."
"Welcome to our home," Drew's father said as he warmly shook my hand.
"It's so good to finally meet you," his mother added as she surprised me with a hug. "We've heard so many great things about you."
Suddenly we heard multiple pairs of feet running down the stairs. I realized that I was also going to meet his siblings, undoubtedly curious about their big brother's girlfriend. In less than a minute I was standing in front of three more smiling faces.
"Hello," I greeted them with a hand wave. I tried again to offer a handshake but was once more taken in by warm embraces.
"We're huggers here," one of his siblings cheerfully exclaimed.
Drew's parents led the two of us to couches. Drew held my hand in his lap as we sat and shared details about our weekend together and our lives back in the city. In turn I learned about his family's shared love of Seinfeld, the Pittsburgh Steelers and the many sports and activities that each of Drew's siblings took part in.
Our "brief visit" ended up lasting a couple of hours, and I was surprised to find myself sad to leave. The genuine friendliness and warmth of Drew's family made it hard to say goodbye.
"Come back soon," Drew's mom encouraged as she enveloped me in another hug. "You're always welcome here."
I felt relieved, happy and hopeful on the final leg of our trip back to the city.
Drew looked over at me and smirked. "I told you they'd love you." He held my hand as we drove on the expressway. "It makes no difference if you're transgender. They just want me to be happy, and being with you makes me happy. That's all that should matter."
There was nothing left to do but smile. He was right.
Today I look at our relationship and feel like we're any other imperfect couple living in the city. Syncing up our schedules has become a balancing act ever since Drew left finance and started cooking full-time at an acclaimed restaurant. Household chores are something we're still figuring out how to divvy up. We also bicker and argue like an old Korean couple.
But our relationship far outweighs any of these challenges. Drew's smile and pun-riddled jokes never fail to make me forget a bad day. Date nights are times that we both treasure and take great care to plan. We also talk about our future and the goals we want to attain together.
On a weekend spent cleaning our bedroom, I stumbled upon a note Drew had given to me a while back. I put down the cleaning supplies and sat at my desk for a brief walk down memory lane.
Toward the end he wrote, "I will always look upon you and the fact that I am a part of your life with the greatest sense of pride possible."
I smiled as tears fell freely on Drew's note. For him I was never the girl he had to conceal from others. I was instead the person he was proud to call his girlfriend. The love of his life.
Drew has helped me truly accept that I am loveworthy, deserving of being loved for all of who I am. He has shown me that I have been and always will be more than enough for someone.
And I am grateful that someone gets to be him.
Images via Shutterstock, Andy Marra.