defeat or get the better of (someone) by being clever or cunning.
"the hero is invariably outsmarted by the heroine"
synonyms: outwit, out-think, outmanoeuvre, outplay, be cleverer than, steal a march on, trick, make a fool of, get the better
When someone trys to outsmart the Urban Dictionary it usually ends in failure. People commonly just mash things on their keyboard and look it up to try and see if it has no results. Little did they know I just looked for a definition of this and I won this little game.
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.