What A 12-Year Veteran Of OkCupid Learned About Love

Dating
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Longest OkCupid User

Jason Hill was in for a surprise when he attended a meetup of OkCupid users in 2009. Sam Yagan, co-founder of OkCupid and current CEO of Match.com, dropped by the gathering and spoke to Hill. When Hill told him he joined the site in March 2004, Yagan was shocked.

“That was less than a month after we started,” Yagan exclaimed. “You must be our longest user!”

Fusion recently spoke with Hill about his status as OkCupid’s longest continual user, and the lessons he learned along the way. His story offers key insights into the world of online dating:

  • Try it if you need to expand your dating pool. Hill initially experimented with online dating because he’d moved across the country. He knew very few people, and those in his immediate social circle were often significantly older. Online dating helped Hill find more compatible dates in nearby cities.
  • It’s helpful if you’re socially awkward. “The great thing about online dating for me was that a person clearly indicated interest,” said Hill. “And once the person indicated interest, I knew the rules, right? At that point, dating became something I could do easily.” Online dating takes the guesswork out of determining interest.
  • It’s never been cool to be a jerk. Today, female daters are used to receiving explicit messages and pictures from men. While Hill can’t say what online dating was like for women 12 years ago, he’s confident that his approach was successful because it wasn’t crude. He aimed for a mix of approachable, forthright, charming, and snarky - never creepy - in his messages.
  • You can’t be in a relationship until you’re really ready. Hill found himself on a steady stream of dates with women who were trying online dating for the first time. They were separated, or in the middle of a divorce, or had just broken up, and weren’t mentally prepared for the relationship Hill was looking for. The moral of the story? Don’t try to force something serious if you’re not ready for it.
  • Profiles are only part of the picture. Some dating services go to great lengths to make comprehensive profiles. Others practically skip the profile in favor of photos. Either way, there’s only so much you can learn about a person through a screen. Meeting in person is essential if you want to get an accurate impression of a date.

Twelve years after he joined OkCupid, Hill is happily married. Although he didn’t meet his wife online, he believes his experiences with the site prepared him to find his perfect match. He credits online dating with teaching him at least one indispensable dating lesson.

“Thanks to all those hundreds of dates I had gone on,” he said, “what I realized is: At some point you just need to say what you want, especially at the beginning of a relationship, maybe even on a first date. There’s no point in beating around the bush.”