Okay, prepare yourselves for a tenuous analogy. In the business of love, there comes a tipping point, after you’ve been chasing the object of your affection for long enough, that will probably define your future happiness or otherwise together. Usually it’s after about three months of fruitless attempts at wooing. It’s the moment when you must choose whether to walk away or try a new line of attack ­ it’s a moment of fear, uncertainty and doubt.

In the business of mergers and acquisitions, things can be pretty similar. It’s now about three months since Microsoft started trying to seduce Yahoo, and the software giant seems to have reached the point where it doesn’t really know whether it’s coming or going. One week, chief executive Steve Ballmer decides to cut his losses and apparently pulls out of potentially one of the biggest deals in IT history; then the next he declares he would actually like to get cosy again, by pursuing some sort of “transaction” with Yahoo.

So where does this leave the two players, and why should enterprise IT chiefs even care, aside from the voyeuristic pleasure they might get from watching a mighty software behemoth make a bit of an idiot of itself chasing after a younger, more exciting, but so-far unobtainable, internet bombshell?

The main reason Microsoft wanted Yahoo so badly was that it believed a deal would have accelerated its software-plus-services strategy, improved its web search and search marketing capabilities, and, maybe, even have allowed it to put an exclamation mark after its name. Okay, maybe not the last one, but the other reasons all make business sense.

Yahoo is number two in the search advertising space with around 20 per cent of the market compared with Google’s 70 per cent. Microsoft is so far behind it can barely see the others, although it is strong in display advertising. And Yahoo’s Web 2.0 savviness would have been a real value-add for Microsoft in its vain attempts to catch up Google in the cool stakes. Finally, Yahoo’s datacentre reach would have helped Microsoft significantly in giving it the capabilities to support a concerted push towards a cloud-based computing model.

Well, that’s what you could have won, Mr Ballmer. But what kind of impact will this affair have on the enterprise? Not a particularly big one, I suspect. The shift to more cloud-based computing may be unstoppable, but it’s likely to be a few years yet before enterprises adopt the model wholesale. Microsoft could certainly have done with Yahoo’s experience and infrastructure to help it here, but that’s not to say it won’t be able to come up with viable web-based enterprise alternatives to its Office suite organically.

One thing that is for sure is that Microsoft can’t afford to sit around and sulk about the rebuff it’s had from Yahoo. Google is making slow and steady in-roads into the corporate market with its Google Search Appliances and Google Apps online collaboration suite. This currently only accounts for about two per cent of its total revenue, according to some calculations, but we should expect the firm to innovate and expand in the enterprise software market in the same inexorable way it has done in areas like web search and search advertising. This is potentially very bad news for Microsoft.

Whether Microsoft tries to see off this challenge by developing cloud-based solutions of its own or through chasing after the likes of Yahoo like a teenager with a crush, there’s always the possibility it will also take its eyes off its corporate software business. More than a little food for thought for IT directors, then.