Breaking Up With Hotmail

Why I’m ending my longest online relationship.

By Jack Shafer

Illustration by Alex Eben Meyer. Click image to eexpand.Hotmail and I go way back. I had an account there before Microsoft bought it for a reported $400 million at the beginning of 1998, which makes the free e-mail service my longest-running online relationship. There were others before Hotmail, of course. I had a CompuServe account, and an AOL address, and before that, way back in the days of my cyber-puberty, I had an MCI Mail account that was so slow you could almost read incoming messages as fast as they snaked their way onto the screen at 300 baud.

My promiscuous relationships have also included corporate mail accounts, usually via Microsoft Outlook. But using Outlook is like sleeping with a hooker at a convention and sending the bill to your boss. There’s no real pleasure to be found in Outlook, no intimacy, only relief. Outlook exists to satisfy your corporate manager and the freaks down at IT, not you or me.

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