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1.
To predict, criticize often after results are know. This normally occurs from a person who you are having a conversion with and is trying to demerit someone else or you.
From Showtime series Weeds Season 3 Episode 7-He Taught Me How to Drive By
Marvin: Are you second guessing me bitch?!
by Askjeeves October 03, 2007
49 31
 
2.
To guess.

Utterly pointless use of the word "second" to convey no additional meaning but with the intention of appearing more intelligent than in fact. Much beloved of political reporters. See also Anytime soon.
The Tories are trying to second guess what UKIP will have as the main plank of their Euro-election manifesto.
by Global Reach My 4rse January 13, 2014
4 3