Will AOL And Yahoo Finally Hook Up Already Or What?

Tim Armstrong and Arianna Huffington
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They’ve been flirting awkwardly and publicly for years without any culmination.

But now that they’ve both had legendarily terrible weeks and could really use some love, geriatric Web company AOL really wants to hook up its fellow legacy brand Yahoo, for real this time.

Bloomberg reports Friday that AOL CEO Tim Armstrong is in talks with advisers at Yahoo about having it acquire his company.

Full Disclosure: I was an AOL staff blogger between January and November of 2010.

Armstrong is reportedly so serious about it that he’s discussing the matter with AOL’s crack mergers and acquisitions team, including investment bank Allen & Co., retained by AOL since at least August 25 and also recently hired by Yahoo to explore the latter company’s best options going forward following the dramatic firing of Yahoo CEO Carol Bartz by telephone on Tuesday.

But Yahoo might still be playing hard to get: CNBC tweeted on Friday that “Source Close To Yahoo Says No Interest In A Deal With AOL.”

That’s perhaps not such a surprise, given Yahoo is worth about $18.2 billion compared to AOL’s $1.6 billion, according to Bloomberg.

Both companies’ travails have been playing out very publicly of late: AOL for its part has been dealing with the dueling egos of its news chief Arianna Huffington and TechCrunch Founder Michael Arrington.

The ridiculous conflict at AOL began with the Sept. 1 revelation that the company was going to be the lead investor in a new startup venture capital fund created Arrington.

AOL acquired TechCrunch for a reported $30 million in Sept. 2010.

At least three conflicting statements from AOL regarding potential conflicts-of-interest and several emotionally wrought TechCrunch blog posts later, Arrington has reportedly been fired to satisfy the whims of Huffington, who sold her own website The Huffington Post to AOL for a reported $300 million in February.

So neither company is looking like it is having particular success re-inventing itself lately.

Still, it’s worth noting that AOL and Yahoo have discussed combining their sagging Web empires into a unified company since at least 2005, only to have the talks stop and restart again and again, though on the last effort, in late 2010, it was AOL that was supposedly mulling a Yahoo acquisition.

There are lots of reasons why a deal would or wouldn’t make sense, according to tech business writers.

But seriously, given the number of “conversations” about the subject, how much longer can the two fight their feelings?

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