Guy No. 37

In 1992, a freshman in college, I wrote my first love note on my best stationery using a blue ballpoint pen. I’m sure it was not legible and, because I was not a native speaker of English, full of misspellings. I hand-delivered it to the young man I had a crush on, having seen him from afar in classes and dining halls. What I remember most was how much courage it took to approach him. Twenty-two years later, at the age of 40, staring at an online dating website for the first time I wondered how the heck I could do this: meet a man digitally.

I was still that romantically awkward young woman who was normally social and friendly but froze immediately in front of a man I found attractive. Growing up, I had no role model to show me how to flirt, look beautiful, be feminine, and—most importantly—build a relationship with someone. My parents fought for as long I could remember and because of his Taiwanese culture, my Dad thought the best option for me was to wait to get a divorce until I became independent at 22. I never even got the dreaded “sex talk” as a teenager because my parents were too busy arguing and making a living as first-generation immigrants setting new roots in suburban New Jersey. So I learned by trial and error with friends.

To be truthful, I didn’t decide to brave the online dating world on my own initiative. A few girlfriends met their husbands that way and nudged me on. “You don’t want to end up alone, do you? How about trying online dating and meeting new people?” At the time, my life brimmed with close friends—all couples and single women. It had been 12 years since my last relationship and I was finally ready to put the effort into meeting someone new.

I figured I would use the same methodology for how I found my primary care doctor, plumber, and condo: word-of-mouth recommendations from my trusted girlfriends.

With my professional background building websites and computer applications, software technology came easily to me. Signing up on a website took zero time but then I sat looking at my laptop screen. I’d created many versions of resumes and kept my professional LinkedIn profile up to date. But now I had to create a profile for dating. How do I present myself, my look, personality, pleasures and desires digitally? And how can I judge a man based on pictures and a few sentences? My awkwardness resurfaced immediately, even though I was sitting comfortably at home alone.

I cobbled several descriptions and photos together into a profile. My best effort. Not good enough, one girlfriend determined. After critiquing my “About Me” section and making a few editorial tweaks, she took new profile pictures of me, encouraging me to look relaxed and happy.

When online messages started coming in, I answered them the same way I responded to work emails. I thanked each man for contacting me, no matter what I really thought about him. My friend came to the rescue once again: “You don’t need to reply to everyone—only the ones you’re interested in. Otherwise, you could send the wrong message.” That made sense: I  didn’t want to be rude, but I also didn’t want to mislead.

In the online dating world, the first interactions are text messages. So instead of checking out what kind of watch he wore, I looked for typos and emoji choices. Rather than seeing how his eyes smiled when he talked, I kept track of how often he texted (some, every hour, others once daily, or even rarely); the size of his text messages (a few words to a couple of paragraphs); and the time it took to go from messaging in the dating app, to asking for my number, texting to each other’s phones and then arranging a first date. Sometimes it took just one quick text chat to get to a time and place to meet, other times, months.

I even created a dating spreadsheet: date (when we first messaged), online handle, real name, a few words about him, source (the website or app where we met), output (how it ended), and our dates (locations). The engineer in me wanted to capture and organize something about all the men that came into my life, even if it was just for a brief moment. For some, texting upgraded to include pictures. When we hit it off, I created a photo album of all the pictures we texted each other along with a snapshot of his dating profile picture. If we texted a lot, I had a document tracking his background, past relationships, or any other interesting things he texted or told me.

Meeting someone digitally flipped how I got to know a man. Instead of seeing him first on campus, in the office, or in a bar, watching him interact with others, my eyes took a back seat from my brain, which took in all the texts. I learned what I called his “text personality” first. Was he clever? Did he have a sophisticated vocabulary? Did he send flirtatious but respectful messages? I knew his age, where he lived, his hobbies and profession. Is he vaccinated? Does he have a passport? Is he a foodie? Kids? Pets? Where did he grow up? School? I engaged him on a logical level first.

So here I am in 2021, seven years after embarking on this digital journey, which includes a pandemic that put a pause on my routine. But I’m back at it. My tracker has 37 men now. And with number 37, I find myself in a situation I haven’t been in for a while: an early satisfying, romantic relationship. I like how he makes me feel about him, me and the world.

At first, I thought we were too different. I work in technology consulting and have always been a 9-5 worker; he’s an actor undertaking various projects with unpredictable hours. He quotes Shakespeare while I’m into Harry Potter and the Twilight Saga. He proudly identifies who is who in Hollywood, yet I rarely watch TV shows or movies. He thinks coffee is gross and I can’t go one day without several cups.

But maybe those contrasts are what make us work. While he reads Frankissstein, I delve into Klara and the Sun. We are both short of bookshelf space and always have a few open books scattered throughout our living spaces. He can rattle off classic jazz musicians like John Coltrane, Miles Davis, Louis Armstrong, Charlie Parker and Thelonious Monk; I’m plugged into my daily fix of Spotify for the latest acoustic cafe or K-pop. We both have a passion for tea, but even there, we have different tastes. I have a drawer full of exotic tea bags such as ginger turmeric, lemon spice and chamomile lavender and his favorites are Darjeeling (chai), Irish Breakfast (Assam), white pomegranate, wild fresh mint tea when camping and moon milk when he can’t sleep. We connect as lovers of books, music, and food—often exchanging our favorites.

Beneath the surface, we’re more alike than what meets the eye. He started his career in marketing in the corporate world but decided to pursue his creative aspiration full-time in his mid-thirties. Though my corporate tech job is important, I spend my free time writing and dream of doing that full-time when I‘m financially independent. Neither of us has or wants kids. We both rely heavily on foot or bike (him) and public transportation and love wandering around our neighborhoods up close and personal. He sends me articles about tiny houses not knowing that I also want one in the future. And linguine with clams, we both love.

Two months in, we’re still seeing each other and texting. I don’t have to track how often I text him. I just do. I ask questions and he answers right away. When the Green B line had a train crash near where I live in Boston, he texted immediately. “Are you okay?” When he canceled one of our dates because of his mother’s sudden emergency an hour before our meeting time—her bathroom’s pipe broke and she was frantic—he texted, “I hope you’re not upset. I want to see you. Just a matter of when.” He likes my enthusiasm. When we’re together, he gives me soft kisses and tight hugs. We cuddled while watching The Chair. “Miss your face and hope to see you super soon!” He just texted. I am cautiously optimistic.

Online dating is part of modern life. But eventually, the digital element ends and the human part begins, blends in and takes over. I’m reminded of that love note I wrote almost 30 years ago: how simple to write it with so much courage. Once you connect with someone, the digital façade goes by the wayside. Each party has to be brave and vulnerable enough to love someone directly.

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