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The pursuit of casual sexual relations, especially a male's pursuit of a female.
"I usually spend my weekends drinking at the bar and chasing tail"
by deorum March 19, 2008
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Jun 24 Word of the Day
An exclamation made when your friends or family are teasing you to a point where you can't handle it anymore and a hissy fit is in order.

Derived from a YouTube user's famed outburst following Britney's lackluster performance at the 2007 VMA's.
Sarah: 'OMG Susan, I can't believe you are wearing the same skirt as yesterday. Oh, and by the way, EVERYONE knows what you did with Kevin on the weekend. Plus you look a little fat, are you retaining water?'

Susan: 'LEAVE BRITNEY ALONE!'
by Billy Chickenhole September 15, 2007
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2
The time-honored Dixieland tradition of tying bottle rockets to the tails of moo cows. This tradition, known by many names such as Firemilk, Paddy Bang, and yes also Chasing Tail, is enjoyed throughout much of the Southland.
Wife: I overheard my husband say he was planning on chasing tail tonight. Is he going to cheat on me?

Husband's wingman: Absolutely not. It's totally about cows.
by Melder_Recorder November 12, 2008
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3
The pursuit of casual sexual relations, especially a male's pursuit of a another male. Sometimes misconstrud that this is it is in the pursuit of a hetrosexual relationship but is not the case.
Guy: What you doing this weekend?
Martin: Chasing Tail
Guy:You looking for some hot cock action then
Martin: Word!
by Youknowwho08 August 22, 2008
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