If you’re getting a screen that says tehre’s a problem with the certificate and there are a few links, one says continue to site not recommended, it’s a certificate issue and just click the continue link as long as you trust the site.
If you can’t connect over SSL to anything via Chrome go into the settings and find the security tab. In there you probably have a ton of stuff disabled, enable anything to do with secure sockets or SSL.
You could also just have a corrupt cookie. Try clearing all of your history, temporary files and cookies, the close out Chrome and re-open it.
These are just some kind of random guesses since I’m not really sure what’s going on. If those don’t work for you try and add some info on what exactly you’re having a problem with, like is it a particular site? Is it others connecting to you? Is is Small Business Server related?