Prior to OKCupid Sam Yagan sold SparkNotes in a multimillion dollar deal. By age 25, he was garnering national coverage as the president of eDonkey, a peer-to-peer file-sharing network with more than 2 million users.

This time, he is making a foray into the world of online dating. To compete against such established players as eHarmony and Match .com, which charge fees to customers, OkCupid's gimmick is simple: It's free. (The firm makes money by selling advertising on the site).

The site is designed to be a social environment that allows users to create their own quizzes with individualized, pinpoint questions like "How much of a Red Sox fan are you?" or "If you were a 'Lost' character, which one would you be?"

OkCupid boasts more than 420,000 "active users," defined as users who have logged on in the past eight weeks. There are 40,000 active users in the Boston area, according to Yagan.

Now, Yagan is hoping that lightning will strike a second time. When they built SparkNotes as a free online site, he and his partners capitalized on what they saw as a weakness in a big rival, Cliffs- Notes. They concluded, Yagan says, "If you put free and better together, you can build something powerful." He sees OkCupid as another test of that proposition.

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