If only these were actually easy to stick into emails, I'd be way more likely to use emoticons on a regular basis. :(

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There's something truly terrifying about a mom who has just learned the arcane secrets of making funny animated faces on the Internet. They should make a horror movie about this. [ Update: You can find Genna on her Tumblr ! You should follow her. Genna - your mom is awesome.]

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The Best Links:

1. Literally, Genevieve Clare
2. Also a Must Read: Mom’s First G-Chat

From the magazine Puck , published in 1881. Someone was way ahead of their time - though the boring description full of long unpronouncable words shows just how far removed they were from the modern (i.e. better) way of doing things. Lulz.

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The Best Links:

1. Puck Magazine
2. An Emoticon in 1862?
3. Emoticon Birthday (Is a LIE!)
4. Hitler Emoticons

The = sign makes a serviceable Hitler mustache - which is all you need to know to begin offending your friends over instant message. Here's a list of historically accurate options to get started with.

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The Best Links:

1. Via URLesque