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Villain under betting the flop is tricky, it can be inducing bluff because most villain expects you c/r the flop with a pair and a draw or AK here. I like your check/call the flop.

However, I'd shove the turn and give AA/KK/QQ tough turn decision, decent players fold those hands here.

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I think people are overestimating how deep we are here. His turn bet makes a pot sized bet left to play. I don't know, I just don't see someone finding a fold here on the turn with hands he was trying to induce a bluff with here.

That being said, given the stack sizes, we don't really have a lot of options on the flop. We can't really float given his strength and our history with him, so I am starting to think this is a decent "bluff" that likely buys him 2 free cards against TT-QQ, if he has AK.