Corporate euphemism for issue, problem, malfunction, or disaster. Used by corporate managers as a lame attempt to appear positive in the midst of major problems.
We are having some challenges with our computers, all data for the last three days was lost and cannot be restored.
by MBAsSuck September 06, 2006
One of the two roles men can play in picking up girls. A challenge is a guy who plays hard to get. He says things like "Do I have to call you?" or "Im not sure if i should be with you". Although for some guys it is hard to do and may feel awkward, it is the best way for picking up girls.

The Challenge is the opposite of the Wimp, which is the guy who calls on the first night and says "I Love You" after the first date. Basically, the Wimp is the guy who will be pussy whipped
"Bro, i told that girl i didn't want her number but I got it anyways. Being a Challenge has really helped me pick up girls easier."
by Sean47 September 01, 2007

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