A male who has the ability to fornicate with essentially any woman he pleases, and usually has 20 or more women in their repertoire. Many times, but not necessarily, the prefix playa man goes in front of said man's name.
Referring to the Jim Carey movie Yes Man where he has to say yes to everything and by doing so, his life becomes far more interesting and enjoyable.
What time did you get home after you left the office?
I was playing 'Yes Man' and ended up dancing at a nightclub with strangers until 2 in the morning.
In sports, making the brazen decision to go for the win instead of the more conservative decision to tie. In American football, for instance, going for the two-point conversion instead of sending a game into overtime with an extra point.
Instead of being a vagina, Steve opted for the manplay and went for 2.