The Freudian Send can get you fired, but it could also get you dumped. Gmail has added a feature — in the Labs, not in full release yet — that tries to give you One More Chance to quintuple-check your recipients before you hit Send.

New in Labs: “Got the wrong Bob?”
Ever included Bob (your boss) instead of Bob (your friend) on an email by accident? Oops! Turn on “Got the wrong Bob?” and Gmail will check if you meant to include Bob Smith rather than Bob Jones based on the groups of people you email most often.

Of course Google can’t say “Ever included Bob (your boss) instead of Bob (online hottie in which you are engaging in a torrid, multimedia erotic extravaganza) on an email by accident?” but you know that’s what they mean.

One caveat: If you’ve ever tried to use Undo or Send Later or any other feature to help you send to the right person, you already know that it does not take long to get so used to the confirmation dialog that you end up clicking it by habit, thus preventing it from preventing you from doing something stupid.

In order for any of these life-saving tools to work, you have to meet them halfway by slowing down and reading the address or addresses in all of your To, CC, and BCC fields. Just like with sex, the technology cannot replace the human brain.