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Originally used for when a man knowingly had sex with a girl, who he knew had some type of std (sexually transmitted disease). He would wear a condom for protection, but the "risk" is that it might fail.
More commonly used when referring to dating (or just having casual sex) with someone you know you will have problems with in the future. The "risk"is the aftermath of the relationship.
"I was going risky with my math tutor class last night, but I think she wants a real relationship. That's gonna be a problem"
by YourKngco December 16, 2011
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