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AUTHOR: Jack Shafer, editor at large at Slate

CONTENTION: Though Shafer once had a good thing going with the e-mail service Hotmail, it's time they went their separate ways

WHY, WHAT HAPPENED? "Somewhere along the way, Hotmail changed. I'll be the first to admit that I changed, too."

OKAY, GO ON: "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."

IS THERE SOMEONE ELSE? "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."

UM--ALL RIGHT: "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."

WOW, THAT'S--"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."

JACK, YOU KNOW YOU'RE NOT TALKING ABOUT AN ACTUAL WOMAN, RIGHT? "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."

THIS IS STARTING TO GET WEIRD: "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."

DOES AN ESSAY ABOUT E-MAIL SERVICES NEED TO BE DRAPED WITH CASUAL MISOGYNY?: "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."

This article is from the archive of our partner The Wire.

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