Winning the College Contest Means Everything Is Rosy, Right?

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Modern Love has held four college essay contests over the last 10 years. We checked in with two winners to see how telling their stories affected their lives.

Caitlin Dewey and her husband, Jason Rainwater.CreditCaitlin Dewey

Caitlin Dewey, “Even in Real Life, There Were Screens Between Us,” 2011.

In 2015, Caitlin Dewey, now a reporter for The Washington Post, joined Invisible Boyfriend, an online service that allows users to design and chat with a virtual boyfriend whose messages are written by company employees. Although Ms. Dewey created her boyfriend for the purpose of writing an article, she came to understand the service’s appeal.

“I did enjoy texting this random stranger even though I did not have the faintest idea who they were,” Ms. Dewey said. “Humans are social creatures — of course we form emotional attachments even in these sort of strange, digital circumstances.”

Turns out that wasn’t Ms. Dewey’s first encounter with an invisible boyfriend. Her contest-winning essay details a relationship that flourished online, then failed in person, in an era before the emergence of dating apps like Tinder and Bumble.

As a senior at Syracuse University, Ms. Dewey was immersed in a relationship with a college student who lived three states away. Every day, they would exchange endless Gchat messages and talk for hours on Skype. One night they even accidentally fell asleep with their laptops open, waking the next morning with their video call still in session.

When the two finally met in real life, however, their interactions faltered. (Ms. Dewey had rented a car and driven nine hours to see him.) They strained for conversation. After spending a disastrous final evening barely talking, Ms. Dewey left, holding back tears.

“I don’t think our relationship failed because it played out online,” Ms. Dewey said. “I just think the internet managed to disguise a lot of flaws.” Within the confines of a screen, Ms. Dewey and her cyberlover presented their most engaging, charming selves, while omitting everything else.

Although that experience left Ms. Dewey suspicious of digital interactions, she decided to sign up for OkCupid when she moved to D.C., a city where she felt isolated. After going on a number of dates, Ms. Dewey met the man who would become her husband; they married this year over Labor Day weekend.

Their courtship was the reverse of her previous experience. “In our online interactions we didn’t instantly click,” Ms. Dewey said. “Our match percentage was really low, our messaging back and forth was kind of stunted. But in person, we hit it off.”

Malcolm Conner, “The Physics of Forbidden Love,” 2015. Here, in his own words, he discusses the essay and its aftermath.

You know how people say, “You write to find out what you believe”? My motivation was to find out why I was staying in a relationship I knew was doomed. Since my girlfriend and I started seeing each other, we’ve kept our relationship secret; I am a white, trans man and she is an Indian immigrant. Her parents only approve of her dating someone who’s Indian, which means she and I eventually must break up.

In writing this, I just realized that our relationship is what it is and that I overwhelmingly wanted to remain in it. I think there are reasons to pursue and value relationships that are finite.

Recently I’ve been thinking a lot about my parents’ divorce. Initially my parents and sisters and I all felt that it was just a painful experience. But we’ve come to understand that this end wasn’t entirely negative — their marriage was still a successful union.

I also wanted to write my essay because I found out that some people on campus knew I was trans, but I hadn’t told them. I worried my control over this information was slipping. I didn’t think I would win the contest, but if I did, I would be able to let people know about my trans identity in my words, in my voice and on my terms.

The response has been very positive, which was a surprise. While I did receive some hateful messages, the majority were really kind.

The two biggest subjects of the essay — my trans identity and my relationship — were both hidden parts of my life. When important aspects of your life remain secret, they start to feel unreal or invisible. My relationship and trans identity not only have been validated, but also made real in a way that had been previously denied.

Miya Lee, a senior at Columbia University, assisted with the last two college essay contests.

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