The cache is too old now and it has not been updated for a long while. There is one reason I can think of that could lead to this result - I made some page's title and meta description identical long time before, but I rectified it soon. Did my website get penalized?
Your best bet is to simply increase the frequency of how often your content is crawled by doing something social bookmarking, dropping links on Twitter, and the like. I've noticed on some of hte larger websites I have that it can take anywhere from af ew days to a few months for old cache content to be updated.
Your webpages' cache information will be updated after the next crawling process takes place. Google's WMT will help you find your website's crawling frequency. If your websites' cache is still not updated even after Google bot has freshly crawled your pages/site, then there should be some code preventing it because by writing certain codes on your site you can request Google not to cache(simply store) your content.
What pradeeps said is write, check your robots.txt file and also submit your site maps to google and other search engines this has helped many webmasters.
I'd recommend that you build more links, and get more fresh content up. Google usually updates those that are updated frequently and they're aware of the new content because of all the incoming links.
Simply reload your sitemap.xml file. Use of twitter or any major social networking site will also benefit.
Try to increase the crawling rate, just a little higher on the GWT of your site, work on my site here..
Google does crawls on regular bases though. Posting to sites that get crawled on regular bases and leaving the link to your site is a good natural option. Those sites would be forums, blogs ect... You could try as mentioned before in responses, setting meta tags to revisit site in specified days time , but by experience those are kinda redundant. Google actually crawls sites on regular bases and actually shows no update in webmasters tools. If servers lets you check visits, you can see that google comes round very often. In fact almost every day at same time. Google shall crawl your site when it finds a dofollow link also, if not crawled before. And no, i dont believe your site is getting a red flag from google, as long it shows 1st when you type in domain name.