For example, when they ask for your email address Microsoft says:
We don't send chain letters, lame jokes, or other unrelated stuff.
And then the sign me up for emails message reads, "Sign me up for the way cool and at most monthly newsletter for webmasters."
Personally, I think it shows humor and makes it feel more inviting. I agree with WebmasterWorld admin, Rogerd, who said:
They're just trying to soften up the old Evil Empire image with a little humor... It's a new fun, playful Microsoft. Think of Steve Ballmer as your best bud... :)
But I guess not everyone will feel that way.
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Forum discussion at WebmasterWorld.