Not sure if someone has said this already but I think the ads on GMail are great. They are completely relevant to what you are discussing. It's like you are thinking about something, and then bam, just look to the right and your answers are there. So what if a machine 'reads' my email, like MSN and Yahoo! don't do that? I mean they have spam filters right? Aren't they reading my emails then? Bah. GMail ads are the best I have seen anywhere.
So what if a machine 'reads' my email, like MSN and Yahoo! don't do that? I mean they have spam filters right?
I think the difference is that they don't provide (indirectly) information about actual content of email to 3rd parties. I'd say it does happen in GMail's case (albeit indirectly), as ability to target ad using keywords from content of emails might allow to effectively determine if particular topics are being discussed in the first place, then tempt people to click an ad, flag them up with permanent cookie and you get the picture.
Example: jealous wife targets keywords representing in her view nickname of a suspected best friend her hubby supposedly cheats with.