I have two people in my contacts list with similar names and email addresses. One of them is a good friend who I email often, including political/questionable stuff. The other one is a high-up at the company I work for.
I frequently ALMOST send to the wrong person, and catch myself at the last second.
I think contacts should have a "confirm before sending?" checkbox. I could check the box for my boss, and it would allow me to confirm or back-out before sending him something disastrous.