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The global dating and matchmaking industry as a whole will generate about billion in 2011, of which about .135 billion will flow from the approximately 1,400 U. dating websites, said Caitlin Moldvay, a dating research industry analyst at Ibis World. Love is never out of style,” said Sam Yagan, CEO of Ok Cupid.com, an industry leader among free dating sites, which was acquired for million last week by — the longtime online dating industry leader which charges - per month in membership fees.