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In the 1800s the abbreviation "wid" is used in city directories.
The first speculation is with a female listed first at an address, the term is used to designate a Widow with the male name following.

For example: Scott, Matilda wid Robert = Widowed?

One contemporary site lists wid = with. Hence Scott, Matilda with Robert.

Which is it?

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Contemporary means "from the same time" and refers to the time of the source material, the 1800s city directories, so modern would be a better word. –  Hugo May 9 '12 at 7:14
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2 Answers

Wid = widow/widower (ref: dictionary.com) is the sense used in your city directory

Wid = with is used as a slang in chat, sms, etc

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Wid= with originated as an internet slang. –  Fr0zenFyr May 8 '12 at 14:49
    
@zpletan: thanks for the edit, looks complete now. ;) 'wid', 'wth', 'wit' are used as slangs for 'with'. –  Fr0zenFyr May 8 '12 at 15:00
    
wth wouldn't work, it looks like "what the heck" –  Pacerier May 8 '12 at 17:48
    
Wid Robert = Widow of Robert (since no-one's mentioned that so far) –  Andrew Leach May 8 '12 at 21:58
    
@Fr0zenFyr: Is "wid" for "with" really Internet slang? I always thought it was regional American dialect and much older. For example, in Philadelphia one can order a "cheesesteak wid", meaning "with onions". It's pronounced and often spelled like that, and my impression is this is by no means recent. –  Nate Eldredge May 9 '12 at 13:18
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Wid means a widow or a widower. Wid (internet slang) also means "with".

Internet slang like "wid" or "dat" or "g8" are short for normal words.

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They are "slang" or "slang words", not "slangs". –  Colin Fine May 8 '12 at 22:59
    
Slang words are considered words too. –  Hugo May 9 '12 at 7:10
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