Formspring: The site for prying questions gears up, but will it grow up?

December 29, 2010: 12:49 PM ET

A year later, with new funding on the way, Formspring.me continues to expand its base of both users and skeptics. In many cases, those are the same people.

By Daniel Roberts, reporter

Formspring home page

Formspring home page

Formspring, the Q&A site that allows users to ask each other questions anonymously, just celebrated its one-year anniversary in November. You may not know much about it, but among a certain set of young web surfers, it's got an impressive following. So impressive, in fact, that the company has "big news" coming in mid-January. A source tells Fortune that the company will complete a $10-11 million funding round led by RedPoint Ventures. (Other outlets have also reported on the deal.) A Formspring PR contact wasn't willing to confirm the investment, but did tell Fortune that this information is "incorrect, but not way off."

Even with fresh funding on the way and nearly 20 million registered users, Formspring has still managed to fly under the radar of savvy social media fans, thanks to its teen-oriented target demographic*. So, Fortune took some time with a few Formspringers, and created an account of our own, to bring you a primer.

Although Formspring representatives declined a formal interview, they did tell us that along with its forthcoming news, the company is re-positioning, and will be "focused on helping people learn more about one another in a new way." Sounds like it's moving away from its current identity: a site focused on letting teens ask all sorts of personal questions of each other through the filter of the Internet. In its previous media kit, Formspring said their site connects people "by one simple thing: curiosity about one another." Indeed, Formspring users visit the site to address their curiosities, but to a casual visitor, they seem to be primarily of an intensely personal nature.

The same media package said that 75% of questions are asked non-anonymously. Yet for the seven users Fortune interviewed, that number was closer to just 8%. The key behind the site is that no account, or username of any kind, is needed to pose questions to a user (though signup is needed, of course, in order to answer questions). One simply clicks through to a user's profile and finds a box that reads: "Ask me anything." Submit a question and it goes into the user's inbox; once it's answered, the question and answer appear in the person's feed, which looks much like a Twitter profile.

A deep dive into Formspring reveals a site that seems dominated by voyeurism—often graphic and deeply personal. Despite Formspring's revised strategy, it's that area of topicality that has likely been the unstated engine to its burgeoning growth rate. Interviews with Formpsring users confirmed that curiosity about one another's sexual proclivities and histories is a huge part of what makes Formspring tick.

"The questions end up being mostly sexual," says Jacob Gardner, a 21-year-old UCLA student, "because that's what people are naturally going to ask about when they can be anonymous." Gardner joined the site five months ago, and mostly uses it during downtime, like between exam periods. "If I have an hour between two tests," he says, "I'll actually go on Twitter and say, 'Hey, ask me some questions,' and link to my Formspring." Back when he joined, the second question Gardner was ever asked was, "Top or bottom?" "I knew this would get sexual in a second," Gardner replied before answering.

Gardner, meanwhile, may already be far older than the typical Formspring user. The site doesn't require any personal information be listed, but from what we can tell its target users are girls like Christy, 15*, a high school sophomore in Massachusetts who declined to have her last name printed.

Christy joined Formspring right at the beginning because, she says, it was a big trend for a while. She says that for a few months, it felt like everyone had an account, but that eventually her school got involved and began checking students' Formsprings by accessing them via their Facebook pages. Christy figured having a Formspring account wasn't worth getting in trouble, and deleted it. Even so, all of her question history was instantly accessible when she re-activated her account to show Fortune some of the questions she once fielded.

The question history reveals why it wasn't a difficult choice for Christy to cancel her account. "The questions were always one of two categories," she says, "either really sexual and sketchy, or mean and insulting."

"Your bikini in your profile picture is definitely a push up bra," wrote someone anonymously (note that it's not even a question). Another simply wrote a crude expression of sexual approval we won't reprint. It's likely the questioners are either sexually charged high school boys or jealous female peers, all of whom know Christy in person, but leapt at the chance to exploit the anonymity of the Internet. "I feel like it's definitely a site geared towards girls," admits Christy. "They're looking to have things said about them. I mean, it's why most girls do most things."

Soliciting anonymous questions may be an invitation for inappropriate language, but young people who have been bullied aren't likely to accept the rationale that by joining, they asked for the treatment they got. In fact, Formspring has already weathered one PR storm back in March, when cruel comments on her Formspring page were blamed as one reason Alexis Pilkington, a West Islip, N.Y. high school student, killed herself.

The 'questions' that were posed to Pilkington might have resembled some other ones Christy once received: "My friends tell me you are a bitch, I always thought you were nice, so now I'm confused, who are you?" This, of course, is a danger of exposing oneself to open, anonymous questions. Anonymity doesn't means the questions don't hurt. Indeed, thanks to the way Formspring pages seem to typically be accessed -- through users' Facebook or Twitter accounts -- the questioner doing the bullying is usually someone who knows the subject in real life, and therefore knows just what buttons to try and push. "That stuff is real," Christy says. "Especially in high school, it's more effective. It doesn't really faze me though." People who are fazed, says Christy, should just log off.

Of course, Formspring is not all bullying. There are accounts where fun, respectful questions like "What's your biggest fear," or, "Favorite book of all time?" dominate the discussion. Also among the anonymous masses are users that happily interact without the cloak of anonymity. Brett Yarchin, an 18-year-old freshman at North Carolina State, is one of those people. Yarchin, under his username, once asked a friend, "How come you're always sick?" to which she replied honestly, "The medication I take for my disease weakens my immune system."

Yarchin also sees more potential in the site. Though he hasn't used it in a few months, he likes the major redesign the site underwent in June. Yarchin also points out that often, anonymity is voluntarily broken: "A lot of the time, it's friends joking with each other; they'll post anonymously but ask something obvious or make an inside joke so that the friend knows who it is," he says. Still, there's a stigma that comes with usage: "It's a site aimed at girls 15-19ish," he suggests.

The trend has caught on to such an extent that there have been cases of college admissions officers using Formspring to answer questions about a school, or, in one example, a rabbi that addresses questions of faith. Kim Duthie, an Australian high school student who recently released naked photographs of two men from the St. Kilda Football Club she accused of impregnating her, has taken to Formspring to answer media questions about her plans and feelings. (The men were cleared of wrongdoing.) To date, Duthie has answered nearly 3,000 questions.

It makes sense, then, that Formspring is only one of many sites that now exist for Q&A. The list includes Quora, Kommon, and Fluther, which Twitter bought up just this past week. Quora, however, shuns anonymity—it almost reads like a Formspring for grownups. With its redesign and new funding, Formspring seems poised to try to evolve beyond its foundations. But as long as the site provides a cloak of anonymity to questioners, especially in an era where online identities are becoming even more closely tied to real life ones, Formspring will be hard-pressed to shake off the salacious questions that drove so much of its early growth.

Again though, Formspring isn't all sex and snobbery. In an account I created to test it out, I found myself asked, to my complete surprise, "Why were you so mean back in high school?" Perhaps the questions just depend on who your friends are, and what they really want to know about you.

*Editor's note: The word tween was used to describe Formspring's users and target demographic twice in this article, which by some definitions can include children as young as 10. Formspring says it does not target users under age 13, who legally cannot sign up for accounts. The sentences have been corrected.

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