Microsoft and Yahoo! seem to hang out in all the same places but somehow keep missing each other.
This has turned speculation over what it will take to get the two of them together into something of a CEO parlour game.
Media magnate Rupert Murdoch said this week he is "mystified" the two have not come to terms.
E-commerce mogul Barry Diller said Microsoft should never have fired a hostile shot at Yahoo! if it did not plan to stick it out.
Yahoo! board member Bobby Kotick joked that he had tried to get top executives from Microsoft and Yahoo! together to play Guitar Hero 4, the hit video game from the company he runs, Activision.
In separate appearances at the D: Conference last week, the top executives of Microsoft and Yahoo! said no progress had been made on a merger, though they were discussing lesser deals.
The two had held abortive takeover talks over a three-month period that ended on May 3, Yahoo! Chairman Roy Bostock has said.
Microsoft walked away from a proposal to buy Yahoo! for $47.5 billion (Dh174.46bn), or $33 a share, after Yahoo! rebuffed it, saying it wanted $37 a share. Then in mid-May, the companies said they had begun talks on an unspecified deal short of a merger.
On Wednesday, Yahoo!'s co-founder and Chief Executive Jerry Yang threw cold water on speculation that they might be edging back into merger discussions.
"Microsoft is no longer interested in buying the company, and we are talking about other things. We definitely have to understand what they're proposing… they clearly have an interest in Yahoo!, and we need to understand more," he said.
In an on-stage interview at the conference, Microsoft Chief Executive Steve Ballmer said talks had broken down largely over price. Appearing with Yang, Yahoo! President Susan Decker agreed price had always been the biggest barrier to reaching an agreement.
Diller, who runs the company behind rival search engine Ask.com, believes a merger of Microsoft and Yahoo! is necessary to gain the scale to take on Google in web search and ads.
Diller expressed surprise at Microsoft's decision to withdraw its offer and "move on" after pursuing Yahoo! at regular intervals over the past two years.
"It seems to me if you fire a gun in a hostile offer, the bullet has to land in the heart," he said in his own on-stage appearance at the conference on Wednesday.
"Otherwise, I can't imagining firing at all," Diller added.
Murdoch agreed, saying that given the original 62 per cent premium Microsoft was willing to pay for Yahoo!, Ballmer should be more patient. "You aim the gun and you fire," Murdoch said, echoing Diller. "They are not used to big deals, so they backed off."
Murdoch's News Corporation has gotten nowhere in its own efforts to talk to both sides in recent months about alternative deal arrangements involving his MySpace web business.
The wily 77-year-old deal-maker ruled out prospects for an alternative deal between Yahoo! and Google Inc to succeed, saying regulatory issues would probably derail such an agreement.
And Murdoch dismissed activist investor Carl Icahn's latest campaign to replace the Yahoo! board in a proxy fight at the company's July annual shareholder meeting as "helpful noise" to Microsoft and a threat that Yahoo! should not bother worrying about.
"That is not serious," Murdoch said. "Look, he wants to make a few hundred-million dollars for himself."
Murdoch's conclusion is that Microsoft and Yahoo! need to lock themselves in a room and put their last respective offers on the table and settle on a deal.
Speaking as if he were one of the negotiators, Murdoch said: "Look, if the deal is complicated, we will clean it up afterward."
Anticipating the flood of free advice from other executives, Yahoo! made up its own joke video in which Yang and Decker are seen being inundated with unsolicited advice from top technology industry chief executive officers, investors and media pundits.
Billionaire Warren Buffett's advice to Yang? "Buy low, sell high."