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
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
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
When somebody have something in his mind and is thinking about it too much time, something that worry him or something that can't solve.

When somebody has difficult choices and has been thinking a lot about them.

Normally the expression involves "for a long time".
I have been chasing my tail about the problem in the department for two days, but I can manage to find a suitable solution.

I have been chasing my tail for three weeks about the holidays and I still don't know where to go.
by Gustavo Muñoz February 16, 2009
tryin to back a female that you had in the past.
Man, that chick dont want you no more. stop chasing your tail
by eagles930 September 30, 2008
When you take an opioid and heat it with a lighter on tinfoil, you have a straw and inhale the fumes from burning the pill, then you take the liquid that was once the pill in the tinfoil and shoot it up.
Lastnight we arrested a guy who was Chasing the Dragon Tail
by Maggie Caetlyn March 14, 2018
A YouTube Tail Chase or YouTube Tail Chase Loop, refers to the endless re-buffering of a video during streaming. With the loading of Youtube videos comes a circle, with smaller circles going around it. This circle icon appears in the middle of the video during the streaming process. These circles look like a dog chasing it's own tail around in an endless circle. YouTube Tail Chase Loops commonly occur when trying to watch multiple videos at once. If a 1 minute video Re-Buffers 5 or more times, then that can be considered a YouTube Tail Chase. And if a 5 or 10 minute video that never finishes playing, because it doesn't come out of the rebuffering process, is then considered a YouTube Tail Chase Loop.
I got stuck in a YouTube Tail Chase when I was trying to watch a clip of some dumb kid who lit himself on fire. It took me 15 minutes to watch a 2 minute clip!!!
by the2ndflood July 22, 2008