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...what dating sites have trouble getting people to upload pictures?

When the site started there weren't very many competitors. They were also unique in the fact that they are absolutely free.

Sites like match.com and the other dating sites at the time (most were bought out by match.com) allow you to search, but messaging costs money. It was the standard model of the dating site for many years.

I don't know how you can say there weren't many competitors. There were tons. You're right about the business models though. But they were all created before Google and similar ad networks. Perhaps that is the major distinction with PoF.

This is very interesting.

What would be some cool ways to for instance gamify dating sites to make it more appealing to fill them with lots of good content (ie photos and profile text)?

Four year old article.

Back then he was still just doing everything himself.