The company I work for uses GMail for our office email, which was not something I was used to but I got into it pretty quickly. It was nice for a change to be able to access work emails from anywhere. Not that I’m desperate to come home every night and see if anything interesting has happened at the office since I left, but it’s let me work from home without hassle, update my boss on some info from two states away, and at least once explain to a bunch of people at once why the A train was making me very late. So after a couple of years of this, I can safely say that GMail = cool.

Recently, though, something unexpected happened that has me wondering if it’s time to rethink my relationship with GMail. As I often do in my job, I had to take a screen shot to send to someone as a way to explain what was wrong with the page I was testing. So as I wrote my notes, I included a little aside that said see attached after I explained the issue in question. As I also often do in my job, when it came time to send the email, I’d forgotten to actually attach the screen shot. Whenever this happened in the past, it would lead to an exchange much like this one:

Programmer: Where’s the screen shot?
Me: D’oh!

Not this week. No, this week, I wrote my test notes and forgot my attachment and sent the email out to maybe half a dozen people when suddenly Gmail itself stopped me with a message that said, you wrote “see attached” but you did not attach anything; do you want to send this email? It was at this point where I wondered if GMail = kinda stalkerish.

So I added my attachment and sent my email and Gmail looked at me with a smug expression that said, yeah, I covered for you this time, but if you continue to slack off like this eventually even I won’t be able to keep your sorry ass employed. And this made me wonder how closely GMail was reading my emails, and if there were any other ways for it to help me out. I mean, I deal with some confidential stuff, so am I supposed to be comfortable with the fact that my confidential email is being shared between me, some coworkers, and GMail? Or should I trust that confidential or not, most of these emails are so boring that they’d put even a computer to sleep? Either way, this just drilled home the point that someone’s always watching us. At least this time it was watching and was willing to help. So maybe ultimately GMail = my new best friend.

Which is why my coworkers are already sick of seeing every one of my emails this week ending with the sentence I really, really want an iPad.

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