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Nowadays, maids are basically a moe stereotype. Otaku characters like Sakurasou no Petto na Kanojou's Ryuunosuke Akasaka, Lucky Star's Konata Izumi, and the Genshiken gang all love maids. Even K-On's Sawako Yamanaka, who isn't an otaku, puts the Light Music Club girls in maid outfits.

K-On girls in maid outfits

For a while, every single show that came out had a maid character, and several shows focused wholly or in part on maids, who may or may not also be androids (e.g. Hanaukyou Maid Tai, Hand Maid May, He is My Master, Koharu Biyori, Mahoromatic).

koharu biyori he is my master hand maid may mahoromatic

It was shockingly difficult to find a SFW picture from Koharu Biyori.

Even shows that didn't have maids were affected: Digi Carat's Dejiko wore a costume which looked rather like a maid outfit, even though she was not a maid, but rather a clerk in an anime store (and actually an alien princess).

Dejiko

My perception was that this all started sometime around 2001, but I never saw how; it just seemed like one day I was surrounded by maids. (Not that it bothered me to be surrounded by maids.) How did this get started? Was there a single show or a few shows that started the maid craze? Or was it always there, and I just never noticed?

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Most of this is a summary of the paper Maid in Japan: An Ethnographic Account of Alternative Intimacy by Patrick W. Galbraith (author of 'the otaku encyclopaedia')

The first maid costume in Japanese popular culture came from the erotic anime series Cream Lemon, part 11: Black Cat Mansion in 1986. (Hiroki Azuma, Otaku: Japan's Database Animals, Minneapolis: University of Minnesota Press, 2009, p. 42.)

It's worth reading the full paper as it's quite interesting.

Galbraith mentions that they maid cafés may have evolved from hostess clubs, but with the new 'moe' and cute appeal that was starting to gain momentum in the 1970s

A game that specifically had maid cafés in it was Welcome to Pia Carrot!! and is usually tied to the start of this trend. Furthermore, the first maid café to be set up was in 1998 , as a special event for the game.

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The first permanent café Cure Maid Café was set up in 2001 and in the years between then and 2011 a massive 386 cafés were set up (although the majority have closed, there still remains many today)

See also: How did the lolicon genre begin in anime/manga? (as it is similarly motivated by cuteness)

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    Galbraith's paper was very informative, though it did get me all depressed about the state of my life after I saw too much of myself in his description of the maid cafes' regular clientele :-> Thanks for the link and another great answer. – Torisuda Jul 3 '15 at 21:20

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