The Great Connection Hunt

Despite what we keep telling each other about how the web should work, are there are some things we should purposely hold back in the interest of letting the user figure it out for themselves?

I’m not talking about cutting out less-important bits in favor of being clear & concise; I’m talking about positioning important parts in a way that allows someone to come to it from an unexpected direction. Ever find out that two bands that you really like have a couple members in common? Remember what it felt like when you figured that out?

Can we create that type of natural connection without alienating people in the process?