Ask.com's latest revamp, unveiled by CEO Jim Safka to the New York Times, attempts to dive deeper into the Web, pulling "structured data," a fashionable buzzword, from sources like TV listings and health databases. Give Barry Diller's scrappy search engine, owned by his IAC conglomerate, this much: When at first it doesn't succeed, it tries, tries, tries again. But you can't blame the market, or users, for finding all this trying, well, trying.Safka's example — a search for the popular tween star Miley Cyrus which yields TV listings for her Hannah Montana show — looks convincing, at first glance. Neither Yahoo nor Google show TV listings in the first page of search results. But Googling "Miley Cyrus TV listings" readily pulls up a page on TVGuide.com. Ask.com's strategy relies on the notion that a small team of engineers and product managers can guess what users want, find the right databases to pull the information from, and assemble it more effectively than the dominant search engine's algorithms. It's a romantic notion of man vs. machine. But I seem to recall John Henry died at the end.

The 50-and-up set form one of the fastest growing demographics of those looking for love online. That nugget of hope, care of former Match.com CEO Jim Safka, comes tucked into Newsweek's Sex & the Single Boomer. While the Youngs, who've been barely weaned off of cruising Facebook for casual sex, may eyeroll at Web 1.0 matchmaking, and the Olds themselves scoff at the profitability of Web-based matchmaking, it looks they're going at it as sure as the kids today, with their Twitter hookups and their 150-mile-radius locally sourced organic condoms. The real difference? Baby boomers got over talking about it decades ago. (Photo via foundphotos)

Lexico, the company behind reference sites like Dictionary.com and Thesaurus.com, has been acquired by also-ran search engine Ask.com, a unit of Barry Diller's IAC, for an undisclosed sum. It will mean an 11 percent boost in traffic for Ask and more revenue for Lexico's sites, as Google had cut a special deal with IAC for a higher revenue share than it would give to the likes of Dictionary.com. Possibly tipping their hand about future moves, Ask CEO Jim Safka told the AP the site was also looking to improve results related to health and entertainment, presumably through more acquisitions. The move comes after IAC's Barry Diller settled a fight with Liberty's John Malone, a major IAC shareholder, over plans to split the company into five different parts.

Before it suddenly wasn't, CEO Jim Safka's plan to save Ask.com was to turn it into a search engine for midwestern women. According to a pair of tipsters, he explained his idea to employees by using this clip of Marge Simpson Googling herself.

Earlier this week, the Associated Press reported Ask.com would become a search engine for midwestern women. But now the "Marge Simpson Plan" — as our Ask tipster calls it — is off. Apparently, Ask CEO Jim Safka changed his mind over the weekend and executives spent all day Sunday scrambling to put together a new plan. Our tipster blames the confusion on Safka's secretive nature, telling us that when he comes into work his office door is always closed. The silence has once loyal employee feeling apathetic and looking for jobs elsewhere.

As Barry Diller curtails both Ask.com's ambitions and its workforce, his hired hand is turning it into the Home Shopping Network of search engines. CEO Jim Safka says 65 percent of its users are female with a high concentration in their late 30s in the Midwest and Southeast. In an attempt to try to get also-ran search site back on track, Safka is laying off eight percent of Ask's employees and "reevaluating" its strategy. "Everything we do will be put through this strategic filter," he says. At last, a search engine that plays in Peoria. The only problem is that even Midwestern housewives know how to Google.

Bloody Diller. IAC's Ask.com has a new CEO, Jim Safka, who was swiftly installed in the place of Jim Lanzone. Lanzone was fired by Barry Diller, according to sources. And so yet another talented entrepreneurial type makes way for a Diller yes-man. The cover story is that Lanzone left to accept a position as entrepreneur-in-residence at Redpoint Ventures — a cozy, face-saving sort of holding tank for CEOs in between jobs.