Breaking up with Hotmail: Why I'm ending my longest online relationship.

Media criticism.
Dec. 1 2010 5:29 PM

Breaking Up With Hotmail

Why I'm ending my longest online relationship.

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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What attracted me to Hotmail? Well, she was free, and she wasn't Outlook. And she liked to go places! Like any whore, Outlook was pretty demanding, stipulating where and when we could connect. When not at the office, I could only see her via VPN and later, when she became obsessed with the danger of catching some virus from me, we could only hook up if I had a valid smartcard plugged into my USB to act as a prophylactic. Hotmail didn't care about that shit. Anytime from any computer was good enough for her.

A search through my old folders brings back memories of all the good times we had together. I remember when I bought ClipMate and sent the validation key to my Hotmail address. How about my registration for CRAYON newspaper? Boy, I haven't been to that site for more than a decade, and you know what? My username—my Hotmail address—and my password still work! It's so much fun to review all those Amazon transactions from the 1990s and recall the memories of a simpler time: a dozen books, those cheap Koss headphones, that Son Volt CD …

Somewhere along the way, Hotmail changed. I'll be the first to admit that I changed, too. When I asked Hotmail if it was OK if I started seeing other free e-mail services, she said she didn't mind. So I grabbed one from Go.com, another from Yahoo, and a second Hotmail address for Slate-related business. I flirted with the Outlook Express client, and much later Thunderbird. I even picked up an MSN address, technically a paid service but comped because Slate was then owned by Microsoft. Like all relationships, Hotmail and I had devolved into a love-hate-coexistence groove. I hated the fact that Hotmail put limits on how many e-mails I could store without paying. I hated the limitation on the size of files I could send. I suspect that Hotmail hated me because I wanted all she provided and more but wasn't willing to pay.

The beginning of the end came in mid-2004, when I wheedled an invitation to Gmail. Google's Web mail service wasn't about limits. I've saved practically every e-mail I've gotten on my Gmail account and have never come close to hitting my maximum. It's not like I ever fell in love with Gmail—even though I got two accounts there, too. I just compartmentalized. I reserved my Hotmail account for online shopping and software registration. I've got a million electronic receipts there, and I didn't want to bother changing my Amazon, Netflix, Go Daddy, Borders, Napster, and iTunes accounts to a new address. So I stayed, rationalizing my unhappiness. I'll bet the same has happened to you, too. They get their hooks into you and you can't break free.

Why was I unhappy? Hotmail, after all, had done a lot for me and never asked for much in return. Well, I just came to like Gmail better. It was svelte and fast and easily searchable while Hotmail was not. Also, Hotmail kept putting on weight with all of its new features—features that I didn't want. It also went through a bewildering set of name changes that spoke directly to its self-esteem problems: Hotmail became MSN Hotmail and then Windows Live Mail and then Windows Live Hotmail. Who do you think you're fooling, Hotmail? We all know you're the same broad we met back in 1996.

I have never been embarrassed to have a Hotmail address—something I can't say about my AOL account. In fact, I wouldn't be writing this today if Hotmail had stuck to being Hotmail. But no, these days it wants to stand between me and the entire Web, monitoring my every step. When I sign on to collect Hotmail, it immediately starts hectoring me to connect my account to Facebook, MySpace, and LinkedIn. It implores me to "Share something new" with people in my network. It begs me to upload photos. Right now, the opening page of Hotmail is alerting me to the upcoming birthday of somebody I don't even know.

I must confess to having once been seduced by Hotmail's little sister, Messenger, which has also gone through more changes than the corner bank. But I've stopped seeing Messenger, too, because she keeps nagging me about having to upgrade. She insists on becoming my videophone, my social director, my file-transfer program, and my butler! She wants to know my mobile phone number, and man, I don't give that out to anybody. She seems incapable of understanding that I just want her to 1) be stable and 2) send instant messages! Quit with the airs, already! Now I use the Web client Meebo for all of my messaging needs.

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