Free Showdown

[The Goober]

Q,

I too, suck at applying the free showdown raise, although I often bet the turn hoping to take a free showdown.

In either case, these are the things that I look for:
-a passive enough opponent to let me get away with it
-some showdown value (obvious)
-some fold equity (not strictly necessary, but it's nice)
-a decent chance of improving on the river (so I have the choice of going 2/3 bets when I improve and 1/2 bets when I don't)

Usually this means something like middle pair with some sort of draw.

In this hand, you have very little fold equity (he'll almost never lay down a better hand), if you are behind you only have 3 dubious outs to improve, and you you could easily get him to lay down a worse hand that he would have fired with again on the river.