FriendFinder Networks claimed more than 445 million registrations across a network of over 38,000 websites. Its biggest sites ranged from FriendFinder.com and Amigos.com to BigChurch.com, and to adult services it did not hide. It also owned Penthouse. In 2010 it booked $346 million in revenue and $71.7 million in operating income, yet still lost $43.2 million. The reason was debt, and in May 2011 it went public to start paying it down.

Penthouse Buys the Dating Web

FriendFinder.com began in 1996 as one of the first online dating sites, started by Andrew Conru. In December 2007 the company that owned Penthouse bought Various, the parent of FriendFinder, and took the FriendFinder Networks name. The deal left the company with a large debt load. The combined company earned most of its revenue from subscriptions and pay-per-use video. The bet was that a huge paying audience could carry the debt.

Ten Dollars to Chapter 11

FriendFinder priced at $10 a share in May 2011 and listed on Nasdaq as FFN. The stock soon fell below its offering price, and the debt stayed heavy. Paid subscriptions faced growing competition from free sites and apps. In September 2013 the company filed for Chapter 11 to restructure what it owed. Its shares left Nasdaq that November, and FriendFinder emerged from bankruptcy as a private company.

Cover: The Cats' Rendezvous, Édouard Manet. Art Institute of Chicago, public domain. Chosen for cats meeting on a rooftop (a rendezvous).