The company hasn't turned a profit since at least 2006, but CEO Anthony Previte said last month that FriendFinder was working with lenders and advisors to refinance long-term debt.
At the time of the August 15 financial statement, when the company reported a second-quarter net loss of $10.3 million, Previte maintained he was confident the debt would be resolved.
But in today's Chapter 11 filing, the Boca Raton, Florida-based company listed assets of less than $10 million and liabilities upwards of $1 billion.
In 2010, the Penthouse owner nearly bought rival Playboy Enterprises for $210 million, but the deal fell through.
"Despite continuing member interest and high volume traffic, the debtors did not make certain payments to the holders of existing first lien notes and cash pay second lien notes which constituted a default under their respective indentures," FriendFinder said in the filing.
Notable deaths of 2014 [PHOTOS]