Answer by Adam Rifkin:
Yes. In 2007.
From Wired Magazine 17.07 (2009) ……. Wired.com/techbiz/it/magazine/17-07/ff_facebookwall
"Larry Page should have been in a good mood. It was the fall of 2007, and Google's cofounder was in the middle of a five-day tour of his company's European operations in Zurich, London, Oxford, and Dublin. The trip had been fun, a chance to get a ground-floor look at Google's ever-expanding empire. But this week had been particularly exciting, for reasons that had nothing to do with Europe; Google was planning a major investment in Facebook, the hottest new company in Silicon Valley.
"Originally Google had considered acquiring Facebook—a prospect that held no interest for Facebook's executives—but an investment was another enticing option, aligning the Internet's two most important companies. Facebook was more than a fast-growing social network. It was, potentially, an enormous source of personal data. Internet users behaved differently on Facebook than anywhere else online: They used their real names, connected with their real friends, linked to their real email addresses, and shared their real thoughts, tastes, and news. Google, on the other hand, knew relatively little about most of its users other than their search histories and some browsing activity.
"But now, as Page took his seat on the Google jet for the two-hour flight from Zurich to London, something appeared to be wrong. He looked annoyed, one of his fellow passengers recalls. It turned out that he had just received word that the deal was off. Microsoft, Google's sworn enemy, would be making the investment instead—$240 million for a 1.6 percent stake in the company, meaning that Redmond valued Facebook at an astonishing $15 billion.
"As the 767 took off, Page tersely but calmly shared the news with the others on the plane and answered their questions for about 15 minutes. "Larry was clearly, clearly unhappy about it," the passenger says.
"Page soon got over it, but Facebook's rejection was still a blow to Google; it had never lost a deal this big and this publicly. But according to Facebookers involved in the transaction, Mountain View never had much of a chance—all things being equal, Microsoft was always the favored partner. Google's bid was used primarily as a stalking horse, a tool to amp up the bidding. Facebook executives weren't leaping at the chance to join with Google; they preferred to conquer it. "We never liked those guys," says one former Facebook engineer. "We all had that audacity, 'Anything Google does, we can do better.' No one talked about MySpace or the other social networks. We just talked about Google." "