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Whisper, an app. where people can anonymously post text over a photograph and have people respond to the topic, is pictured in Toronto on Tuesday, August 26, 2014.

Matthew Sherwood/The Globe and Mail

Facebook and Twitter may still be the preferred place to hang out on the Web for many, but for those sharing their deepest secrets online, Whisper is the place to be.

The Whisper app is gaining popularity as a way for anonymous users to post one-sentence confessions laid over top of an image.

"Tried to flirt with my husband," begins one Whisper. "He responded by looking like a question mark," it concludes, with the text over top an image of a face-palming statue.

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Many face-palm moments are shared on Whisper, but also some touching and poignant ones. When North American cities celebrated Pride parades in late June, the site featured confessions that ranged from the difficulty in coming out to how Pride allows people to feel more like themselves than any other time of the year.

Michael Heyward, the 26 year old chief executive officer and co-founder of Whisper, says that Whisper fulfills an online need for a much longer tradition.

"Identity and reputation management has existed for thousands of years," he says by way of giving perspective to sites like Facebook and Instagram, where people share the best version of themselves.

"And there's always been places for confession too," he said in an interview with the Globe.

The growth of Whisper shows that people do want to share confessions, or read about others. The site gets around three billion page views a month, and touts high engagement. The company claims that every day, 45 per cent of users upload a Whisper, and the average user spends 25 minutes a day on the site.

The numbers impress investors. In May, Whisper received another round of venture funding, worth $36-million (U.S.). In total, it has raised $60-million, and the latest funding valued the company around $200-million. The company now boasts about 50 employees.

The company's potential was impressive enough to lure Gawker journalist Neetzan Zimmerman to join the anonymous sharing site as its editor-in-chief in January. It was a coup for Whisper, which learned about Mr. Zimmerman's viral wizardry through a December profile in the Wall Street Journal.

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Mr. Zimmerman does not see Whispers as inherently viral, and his challenge is to find the universality in them.

"They're very personal. Every person writes a Whisper with something deep and personal to them," he says.

"The challenge is figuring out how to take something personal and make it relatable to a much broader audience."

In the hopes of building a broad audience that goes beyond its younger demographic, the business is exploring ways to share the Whisper format with other media platforms.

The company signed a content-sharing deal with website Buzzfeed in March, and another one with the broadcaster Fusion in June. It's Mr. Zimmerman's task to cultivate these partnerships, and he says his goal is to get enough mainstream outlets on board that the hidden stories on Whisper do not go overlooked.

"There could be something flying under the radar of mainstream media that can only emerge under the cloak of anonymity," he says.

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While most of the content on Whisper veers towards the trivial and banal – it is, after all, on the Internet – serious content has occasionally emerged too.

Mr. Zimmerman mentions soldiers using it to share the challenges of living with post-traumatic stress disorder. People in Ukraine, Iraq, and Gaza have used the site in recent months to share conditions on the ground.

When American Apparel CEO Dov Charney was ousted in June, a source close to him shared a Whisper alleging that the board already knew about his reported transgressions, and the move was "purely financial." The Whisper was shared with Buzzfeed, which published an article based on it.

"One great thing," he says of the work the team does at Whisper, "Is that we get to tell the stories no one else does."

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