As some of you know, I’ve had a couple of brush-ups with wayward emails in the past. One embarrassing incident involved inadvertently sending an email meant for my husband to my boss.  Another time, a group email I sent out to plan a family birthday celebration included a client’s email address instead of my sister-in-law’s. They both are named Amy, and I didn’t catch the fact that Gmail’s auto-complete function had supplied the “wrong” Amy from my address book.

Now the Internet behemoth Google promises that it can save me from my errant ways by activating the new Gmail add-on “Got the Wrong Bob?”. If an email address in a group email looks out-of-place, Gmail will flag it for me.

I don’t know if I’m gratified or creeped out.

I remember the first time Google’s awesome technology reminded me of Big Brother. When I started using Gmail, I noticed that if I dashed off an innocent email to plan a Girls Night Out, the sidebar on my screen would show ads for entertainment options. If the next email complained about a poor night’s sleep, the ads would change to entice me with a new mattress or other sleep aids. Initially, I had a twisted fascination with the ads Google decided I needed to see. Now I simply ignore  them.

If you’re interested in the latest and greatest email tricks from Gmail, check out the official Gmail Blog. Learn how Gmail can prevent you from sending ill-advised emails to old loves or former bosses after a night of drinking. Gmail Goggles makes you solve a few math problems to prove you’re in the “right stage of mind” (i.e., not too drunk) before you’re allowed to hit “send” after a certain hour.

How do the Google geniuses come up with these things?!?!? Thoughts?

And thanks to Wise Woman Maya for looking out for me and bringing “Got the Wrong Bob?” to my attention!