The messy, non-taxonomical, distributed nature of information on the web really makes some kinds of searches hard. For instance: is there anything interesting (to me) happening in my local area this weekend? Well, your first problem is that all the information for "my local area" is scattered across the internet under a lot of very different names. It might be filed, by some people, under your suburb name, or the name of your county, the name of nearby suburbs, or the names of streets. It might be filed specifically under names of local businesses or venues, or vague colloquial descriptions of nearby geographical or man-made features, such as "the cliffs" or "main street". So even describing your local area can be a challenge.
But we aren't even nearly done yet. Assuming you could pull all that information into one place, it's still a mess, because half of it is not described properly, some is misspelled, some is mis-dated and some of that information has changed since it was put online and nobody bothered to update the website. So good luck even telling what's going on.
Then there's the problem of figuring out what's interesting to you. If you can accomplish the herculean task of gathering and correcting all the information about events in your local area, you still might not stumble upon something that's interesting to you, because it's buried under tons of other information that leads you astray.
Mokalus of Borg
PS - And that's why I don't know what I'm doing next weekend.
PPS - I don't think there's a good solution for this.