Limping/Spewing with 55

Preflop fine...I'd call the raise just to see but I'm trying to hit trips

Flop - perfect you at least got a draw. Depending on action I'm check calling. There is no way I'm leading because I want to see a cheap turn at least.

3bet is spewing, especially since you already have a SB who is willing to call the reraise cold

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I bet out with my OESD, and get raised by the PFR which is pretty standard for him

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Seems like if you thought this was standard procedure for this guy then you would definitely not want to lead out. I don't think you are hurting yourself if it checks through and give a free card. By allowing him to raise you force 2Cold to the SB.