1. Someone who doesn't care what other people feel. Usually used in a sense of REVENGE!!!!
2. A very good song by Kanye West.
1. O-M-G! Did you hear? Jake dumped Ash for Courtney because Ash had a zit! What a heartless SOB!

2. In the night I hear 'em talk, the coldest story ever told,
Somewhere far along this road he lost his soul
To a woman so heartless. ~~Kanye West
by Catsoup June 13, 2010
Somone who has never loved before, and has tryed so many times to do so. They eventually realize love is a wasted emotion.
I am heartless...
by The heartless wonder. February 20, 2010
Heartless are interesting creatures. Created from the bodies of those who have lost their hearts, they have one purpose: to destroy the gate to Kingdom Hearts, thus overflowing the Four Planes of Existance with Heartless. The Heartless come in many varieties, but are most commonly seen as Shadow-types.
"Those without hearts... I shall call them Heartless." -Ansem
by FinalHazard March 30, 2004
treating what others say like they are robots
Man: it felt like it meant that she liked me.

Woman: but you don't know; it could mean anything.

Man: but I've had experiences...

Woman: can we change the subject.

Man: what? Now?

Woman: I know I've been heartless.
by Enrique Wilson April 10, 2015
the embodiment of all that is wrong with society
wow i really love heartless
by dave March 21, 2003
a grimy street rapper from long island new york.... the absense of faith or morals
i just downlaos the new heartless track from www.geocities.com/nyhc4life454
by dave March 21, 2003
when someone does or says something that is mean or similar
if i said that amy was a whore then i could be described as 'heartless'
by Mizzle February 23, 2004

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