For advertisers, finding a way into the hip, unpredictable world of social networking is a lot like being the new kid at a raucous frat party. Where do you fit in, how do you avoid rejection, and where do you run when the police come?

Tens of millions of youthful bloggers constitute the biggest block parties online, showing up on popular networks like MySpace, FaceBook, Xanga, and MSN Spaces. Even Carson Daly and Tyra Banks have MySpace sites, and Xanga brims with "blogrings" for Brad and Britney.

Yet ad models supporting these sites remain uneven. Media buyers typically avoid ungovernable user-generated communities. Google's Orkut and Yahoo's link-sharing del.icio.us have no ads. Drill beyond the main hub pages at Xanga and MySpace and the blog pages carry low cost-per-thousand network runs. It's the same old story, says Paul DeBraccio, CEO, Interevco, who built ad teams in the 1990s for first-generation online communities GeoCities and Tripod. "The No. 1 issue was not having control or censorship over the content," DeBraccio says. "I don't think much has changed."

Strike Up a Conversation

Two things are changing quickly, though: The sites are now too popular to overlook, and advertisers are finding ways to engage user-generated communities. "They understand the environment is a sensitive one, but it's very important to reach this audience," says Jeff Marshall, senior vice president, managing director, Starcom IP. Big brands still worry, but Marshall does sell clients into MySpace, FaceBook, and Yahoo 360. He tells reticent marketers that they can learn from the ways their brands are discussed and even slammed. "It's going to happen whether you like it or not. At the very least, we are encouraging clients to go out and observe the dialogue around their industry," Marshall says.

"To some extent advertisers don't have a choice," says Bob Hiler, vice president of advertising at Xanga, whose ad revenues increased tenfold last year to constitute two-thirds of the premium site's income. "It's a seismic shift in the way this generation consumes media," Hiler maintains.

"Marketers don't realize they can't effect change if they are not part of the conversation," says Colin Digiaro, senior vice president, sales and advertising at MySpace, which dwarfs other social networks, with more than 35 million unique visitors and nearly 55 million registered users. "We educate the advertiser on what this changing culture is and how MySpace has changed it," he says. Edgier music and TV properties, especially, find support here. The official "Family Guy" site has more than 800,000 "friends," and even TV talk show host Carson Daly attracts 27,000.

Despite all the recent reports about sexual predators cruising MySpace and bawdy posts by underage users, the company says it has made progress in broadening the advertiser base to major brands like Target and Procter & Gamble. Executives admit, however, that the company has been too slow in responding to bad press. "We haven't promoted what we do in the area of safety, which is something that will change," says Shawn Gold, senior vice president, marketing. MySpace plans to appoint a "safety czar," launch an education campaign with schools, and create public-service announcements to encourage kids not to reveal their contact information, among other changes.

Weaving Into the Crowd

Rather than blast banners around any old blog post, major brands find safe entry into social networks with custom campaigns that engage the community, yet still control some of the terms. Verizon Wireless is going after unsigned music groups in MySpace with a "Calling All Bands" contest that will put the winning group on its mobile Vcast Music service. "You have to be careful," admits John Harrobin, vice president, advertising and digital media at Verizon Wireless. "But our content is so relevant and so organized in the context of MySpace, we're not necessarily concerned."

Social networking sites offer huge numbers of people who are seemingly more involved in creating their own media than consuming it, which forces marketers to learn new terms of engagement. Marketing on social networks requires more insight into audiences' mindsets and an ability to plug seamlessly into conversations. "We come up with really creative ways to invite ourselves in and provide some value as part of the environment," says Marshall.

The smart way in seems to be the side door. The key is not to promote so much as facilitate, as well as provide people hip and humorous tools for expressing themselves. For Buena Vista, Xanga created fictional blogs written by the main characters in the 2005 movie "Hitchhiker's Guide to the Galaxy." The promotion worked well because members embraced the blog's playfulness. "Our experience has been that if you capture the authenticity of the character, it works well," says Xanga's Hiler.

Wendy's has a small logo on a MySpace profile for its square burger, but the clever videos and downloadable instant messaging icons for this mock "Square" character attract nearly 100,000 members. An appropriately outrageous promotion for Fox's "Date Movie" actually lets the "Hitch" character "pimp" a MySpace profile with a new skin. Fox attracted 25,000 friends the first week. MySpace also helps brands craft content areas ("profiles") and use banners at the site's entry page or a user's personalized home page to promote the most enticing segments. The sponsored content grows legs if users sign up as friends of the brand and it starts "walking" into new social circles.

"Advertisers want to find a way to get involved with the blogs," says DeBraccio, "but it's a limited list that will find them attractive."

Starcom IP's Marshall is bullish on the networking platforms, which he says work well for gaming and entertainment clients. Still, despite the massive traffic, only "a very small fraction" of Starcom's spending goes to social networks. "It's only right for particular marketers that want to reach that audience."

As the format evolves, networks will be less willing to risk alienating users by policing content. After all, most of these sites are defined by their willingness to host free self-expression. Advertisers seeking the notice and respect of visitors to networking sites will need to learn how to mingle. Parental and media shock over what goes on at these kids' parties will continue, but the equation for advertising isn't new. "It's the same decision marketers have been making for years," says Marshall, adding, "Do I want to be on 'The Man Show' or the ABC family movie?"