NEW YORK (TheStreet) -- Ask.com's  Q&A platform Ask.fm allows its 180 million monthly unique users to ask questions anonymously, an important feature in the site's success to date and one that could breed trouble for its new parent, InterActive Corp (IACI) ..

Internet trolls, the ruthless attention-seekers which hide in the shadows of the anonymous web, have been able to grab more and more headlines recently. Days ago, a faceless hacker published photos of naked celebrities, including Jennifer Lawrence and Kate Upton, after infiltrating their Apple ( AAPL) iCloud accounts.

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Time again, the option of online anonymity allows inhibitions to lift and ugly behavior to surface, with Latvia-based Ask.fm already having its own scar. In Italy earlier in this year, a 14-year-old suffering from depression reached out for support from the community only to be inundated with hate-filled messages. The teenager committed suicide in February.

Since then, the site implemented report, block and delete features, but with around 40% of the site's users aged 18 and under, the potential for future trouble is rife.

Read More: Ask.com CEO Doug Leeds on Entering the World of Anonymous Apps

Ask.com CEO Doug Leeds remains optimistic the company, widely regarded as Ask.com's entry into the social and mobile space, can safeguard the platform while maintaining what made it so popular to begin with.

"In the past it had very much operated as a place for free speech where people could say whatever they want. We don't think that's the right approach," he told TheStreet. "There really has to be a safety-first approach."

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