When a Dating Dare Leads to Months of Soul Searching

At 2 a.m., two blocks from Chinatown, Sarah ended our first date by telling me that my race might be an issue.

What was supposed to be a one-hour coffee date had evolved into a nine-hour marathon. From discussing the five love languages during dinner to telling stories about our exes at Coit Tower, we didn’t even notice that we had traversed four San Francisco neighborhoods and logged 10,000 steps.

We had a lot in common, having experienced what some might describe as all-American upbringings. Born and raised in America’s former Wild West (she in Texas, I in Colorado), we had read “Little House on the Prairie” and learned to square-dance in cowboy boots. We’d both spent time on the football field — she in the marching band, I as a strong safety. She loves country music and, well, I don’t hate country music.

Over dinner, we connected when we opened up about our strained relationships with our mothers and how we came into our own when we went to college out of state. Our thoughts and values mirrored each other, as did our Myers-Briggs personality types. Then, as we strolled to the front of her apartment building, Sarah said, “I have to tell you something.”

I smiled, expecting something from one of the countless jokes we had shared that day. Instead, she said, “You’re the first Asian guy I’ve ever gone on a date with. I’m not sure how I feel about that.”

After talking nonstop all day, I was at a loss for words. Because here’s the kicker: Sarah is Asian-American. Her parents immigrated from Taiwan. Mine came from mainland China.

“If things don’t work out,” she said, “would it hurt your confidence?”

“Hey, don’t worry about it,” I said. “I’ve got enough confidence for both of us. When my friends ask what happened, I’ll say, ‘She had everything going for her, but sometimes things get between people.’” I smiled. “‘Like racism.’”

She gave a halfhearted laugh. “I’m sorry. It’s not that I don’t like Asian things. I love all Asian food, even stinky tofu. It’s just that I’ve never really been attracted to Asian men. I think it’s because there weren’t a lot of Asians in my small Texas town. All the Asian men I knew were either my friends’ dads or like nerdy brothers to me.”

It was as if she were swiping right on the parts of her heritage she liked and swiping left on the parts she didn’t.

I knew Sarah wasn’t unusual when it came to these preferences. It’s shockingly common to come across profiles that say, “Sorry, no Asians.”

Maybe Asian men need better representation. When I was growing up, there were no mainstream movies like “Crazy Rich Asians” putting a spotlight on attractive Asian leading men. There were no all-Asian boy bands like BTS gracing the cover of Time and winning over American teenagers on “Saturday Night Live.”

With Sarah’s admission, the last nine minutes of our date undid the previous nine hours. You hear stories of people being catfished by fake online profiles. My date was turning into a catfish tale of its own; I was out with someone who had revealed herself to be completely different from who she first appeared to be. I wondered: Is this actual racism, or, even more pernicious, internalized racism — a form of self-hatred?

“I grew up believing Asians weren’t desired,” Sarah said. “I just wanted to fit in, but my friends had a hard time understanding my parents, and our house didn’t look or smell like my friends’ homes. Whenever I complained about how different we were, my parents would just remind me that despite my efforts, people will always treat me like I don’t belong.”

Her saying that clarified something for me. Despite our similarities, we didn’t have the same experience growing up. I was never in want of attention; in fact, I probably received more because I was one of the few Asian students in school. I could be embarrassed by my parents’ broken English at parent-teacher conferences, but what boy isn’t embarrassed by his parents? Most important, where Sarah’s parents warned her about her Asian identity, my parents celebrated ours. We were proud to be Asian in America.

Rather than seeing Sarah’s revelations as a red flag, I found them to be honest and vulnerable. And I felt as if I were uniquely suited to understand her predicament. Even though society views us as the same, Sarah grew up thinking being different was a weakness while I grew up thinking different was a strength. As a whole generation of minorities come of age in minority-majority America, I wondered how many other people were grappling with this issue.

I was still perplexed, though. How did we match on the dating app in the first place? She had to swipe right, and I certainly had not become Asian overnight. “So why did you go on a date with me?” I said.

She exhaled and looked at me imploringly. “Because my friends dared me to go on one date with an Asian guy. And you’re not what I expected. I realize how horrible this sounds, but I guess I, too, feed into the Asian stereotype.”

We were standing awfully close to each other. It occurred to me this was probably her closest romantic encounter with an Asian man.

I reached out and held her hands. “I think I understand. You really want to kiss me, don’t you?”

She smiled and half rolled her eyes.

Figuring I had nothing to lose, I leaned in gently and kissed her.

She kissed back but then pushed me away and started to reach for the door.

At that point, I didn’t know what to think. Was she rejecting me as a dating formality, or because my race made us an impossibility? I felt indignant. Shouldn’t I reject her outright on behalf of all Asian men?

No.

One of my favorite movies is “Before Sunrise,” where two strangers meet on a train, go on an extended date across a city and begin to fall in love. Celine, the female lead, talks about how when we’re young, we believe there will be many people we’ll connect with, and how only when we’re older do we realize it happens only a few times.

I may have been just 31, but I was old enough to know that this was one of those times.

I thought (hoped!) Sarah felt the same thing, but it seemed my race was keeping her from recognizing it. One night of flirting could hardly undo years of assumptions she had embraced about what is desired. I had never connected so deeply in one date as I had with her and felt thwarted by forces beyond my control.

First dates, by their nature, are not safe spaces. We’re made to confront our preferences and prejudices, whether they be about appearance, race, body shape, intelligence or anything else. One thing was clear, though: As I heard the click of the door opening — the door that would shut me out of her life — I realized I was mistaken about me having enough confidence for both of us.

But she didn’t go inside. She stopped, holding the door slightly open. Then, almost as quickly as she had stepped away, she turned around and, with a sly smile, planted another kiss on my lips.

Many months later, after more dates, kisses and moments of vulnerability over stinky tofu, we decided to get married. On Aug. 31, 2019, we will be tying the knot in my home state.

Sarah thought she knew how she wanted her life to play out. She thought she knew what kind of person she would find attractive and marry. We all do that to some degree, whether those expectations involve race, career choice or the number of children we want. That Sarah was open to examining those assumptions (even encouraging and helping me to write about them) was another quality that drew me to her.

Our childhoods shape us. I hadn’t fully appreciated how Sarah’s had shaped her. Now, at least, we can shape our future together.


Andrew Lee is a venture capital investor at Initialized Capital in San Francisco.

Modern Love can be reached at [email protected]

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