March 3, 2011

Matchmaking math:
1 + 1 = $50 million

By J. Hemmerdinger
Staff Writer

You don't need to be a dating expert to be smooth in the business of matchmaking.

click image to enlarge

South Portland native Chris Coyne, left, hangs out in 2008 with Sam Yagan, one of the other founders of an online dating site.

Radar Online photo

Just ask Chris Coyne, the South Portland native who co-founded In its seven years, the online dating site has attracted millions of members and the attention of a multinational corporation, IAC, which bought OkCupid last month for $50 million.

Coyne, 33, who now lives on the Upper West Side of New York City, said he struggled with dating in high school.

"I basically dated none in high school, and some in college," said Coyne. "Maybe if I had dated more ... I wouldn't have to have started (OkCupid)."

Coyne, who's now married and has a 1-year-old daughter, attended South Portland High School, where he cultivated an interest in mathematics.

Coyne's brother, Dan, who works at the Maine Center for Economic Policy in Augusta, said Chris was a "math whiz" in high school and a gifted writer and thinker with an entrepreneurial sense.

"I had no doubt he would be successful," Dan Coyne said of his brother. "It was just a question of what he (was) passionate about."

After high school, Chris Coyne attended Harvard University. In January 1999, just months before he graduated with a degree in mathematics, he started building, a website tailored to younger readers with a mix of content, including e-cards, personality tests and humorous science projects.

A few months later, while other students were headed south for spring break, Coyne and his friends Sam Yagan and Max Krohn began work on, a site providing free online study guides for students.

The partners sold both websites to publicly traded iTurf in 2000. When iTurf's stock crashed shortly after, the partners helped the company sell the sites to Barnes & Noble, which eventually shut down but maintained

In 2003, Coyne, Krohn and Yagan moved to the next project, a free online dating site that they called OkCupid and launched in 2004.

Unlike its competitors and eHarmony Inc., OkCupid is free to subscribers -- advertisers pay business costs. Coyne is OkCupid's creative director, coming up with new product ideas.

David Evans, an industry observer who runs the technology and branding consulting firm Digicraft and edits the blog, said the success of Spark and OkCupid earned Coyne and his partners a reputation for creating profitable online businesses supported by advertising dollars.

Coyne said OkCupid, based in New York City, attracted members in cities with many young, single adults, like New York. Membership growth has been slower in smaller cities like Portland, he said.

Today, the site has 1.3 million monthly unique users and 500,000 daily users. Coyne said 21,000 Mainers logged into OkCupid last month. He declined to discuss annual revenue, but said the company was profitable in 2010 and will likely be more profitable in 2011.

Coyne attributed OkCupid's success partly to complex mathematical algorithms that match members with like-minded singles.

When OkCupid users sign in, they are prompted to answer a series of questions. Some are quite personal, such as, "How messy are you?" or "How frequently do you bathe or shower?"

Others address politics, religion and sex. There are even math questions, such as, "What is next in this series? 1, 4, 10, 19, 31, _."

OkCupid also asks members how their ideal mates would answer the same questions. And users can rate the relevancy or importance of each question.

Coyne said computers evaluate the information and match members based on compatibility, or their likelihood of hitting it off. The process, which includes millions of computer operations, happens in one-twentieth of a second each time a member searches for dates, Coyne said.

(Continued on page 2)

Were you interviewed for this story? If so, please fill out our accuracy form

Send question/comment to the editors

Further Discussion

Here at we value our readers and are committed to growing our community by encouraging you to add to the discussion. To ensure conscientious dialogue we have implemented a strict no-bullying policy. To participate, you must follow our Terms of Use.

Questions about the article? Add them below and we’ll try to answer them or do a follow-up post as soon as we can. Technical problems? Email them to us with an exact description of the problem. Make sure to include:
  • Type of computer or mobile device your are using
  • Exact operating system and browser you are viewing the site on (TIP: You can easily determine your operating system here.)