It's when you do something that is going to lead to something else that COULD be regrettable. Usually something perverted.
Another more simple way of putting it is, something
lame,
retarded, sketchy,
stupid, not kool and yadda yadda.
Steff is hanging out with her retardedly
hot friend next week....that's Bobo
Steff's phone's is breaking on her. steff's phone is being Bobo.