I don't think he ever folds a set to a 3bet on this board texture against you as the PFR and with the aggressive tendencies of both you and him but I would want to make the sizing so that he continues with his FDs as well. I think 2.5x his raise will let him continue giving him 3:1 on a call.

3bet him, he will think you have an overpair and he's stacking you with his set. Profit!

If sets make up a significant portion of v's range I think you have to 3bet here. You are oop, relatively deep compared to the pot and v has a reasonable chance to outdraw you (yet you wanna play for stacks). All bad for slowplaying.

Based on your description of v, he sounds like a tight and competent player. I can't see him having 2 pair or the nut straight here. More likely set and FD (maybe overpair and pair+straight draw?). I don't see sets or FD's going away from a 3bet, plus you give him the chance to come over the top of you and if not, make it harder for him to get away on future streets

Grunch

I think anything but 3-betting here is wrong and fancy play syndrome.

You weight villain's range to primarily sets and your perceived range is an overpair. Dream flop. Build the pot and get it in OTT if he doesn't put you in OTF.

3b flop to $185

Thank you everyone for the input so far. There were a number of circumstances that made this hand unique, and I'm grateful that players with more experience/skill than myself have offered their analysis.

I'll post results some time tomorrow. FWIW, I'll mention two ways I was looking at the hand that I can now see as less correct:

1. I can get value from a wider part of villain's range by flatting and then CRAI on the turn.
- One example of this is if villain holds 88-JJ, flatting and seeing a blank may get villain to b/f $120 on the turn, i.e. I make 40bb that I would fold out with a 3b OTF. Aside from the fact that overpairs probably didn't constitute a big enough portion of villain's range to target, I think I greatly underestimated how villain would perceive a b/3b from me. In game and immediately afterward I thought the 3b would cause V to go from perceiving my hand as mostly overpairs (i.e. as little as 66+) to mainly sets/straights along with very strong draws (Ad6d, etc). I was worried about him folding hands like two pair and some flush draws. Now I can see that from his perspective it's pretty difficult for me to hold either of the straight combos or a set. It's very easy for him to put me on an overpair and shove with his two pair/sets, and he might even decide to semibluff against overpairs by 4betting his flush draws as well.

2. If I get stacks in on the turn, my equity goes from 64% to 77%. This aggressive villain will probably bet a lot of turns with his range. It may therefore be worth it to take the risk of a bad turn in order to increase equity.
- I really underestimated the number of bad turn cards for both of our perspectives. Any board pairing other than the 3 will cause me to wonder whether I still have the best hand. It's unlikely that V will love any , A, 4, or 6, and there's some chance he may even check back K/Q/J if he thinks I played an overpair and hit set over set. The extra 13% equity just isn't worth this risk.

The other problem in waiting for the turn is that a decent villain knows his equity plummeted, and stops putting money in the pot. So "the risk" you mention isn't just about bad cards for you, it's about bricks for him, too

Results:

I end up flatting the raise. $177 in pot.

Turn: 2 3 5 2. Hero checks, villain looks at the board with a furrowed brow for six seconds before checking back.

River: 2 3 5 2 8. Hero checks, villain checks back. I table the wheel, villain mucks and says he had turned three pair. Said he put me on an overpair and thought that the turn counterfeited him and that he thought I would regard it as a good card if I realized he might hold two pair.

While I agree that a 3b OTF might have induced a shove from a large portion of villain's range (which makes it the best play), the one thing I still wonder about a bit is what I do if I had hypothetically 3b to $185, saw villain call, and then saw the board pair on the turn. I don't think I could continue betting for value effectively against villain's range (losing to flopped sets, flush draws might not continue to draw, overpairs may have already folded flop, etc). As it turned out I checked the river hoping villain might bluff his missed draws. If I check the turn after 3betting the flop I think it might become obvious to many opponents that I have a hand that didn't want the board to pair (either that or I have a set that just filled up and am waiting a street to bet); so checking the turn might have given villain a good opportunity to push me off the best hand, though I'm not sure about that. He obviously didn't attempt to do that when he thought he had a counterfeited two pair facing an overpair.

So that's a hypothetical I'll put out there: If we 3b to $185, villain calls, there will be $417 in the pot. $251 behind.

Turn 2 3 5 2. Hero ??? (Thinking only options are shove, x/f, x/c) If hero checks and villain checks behind, what is the plan for the river?

Turn would be an obvious shove if called. V is almost always shoving flop with a set, and you still beat all overpairs so get it in for a little over half PSB.

congrats, you won the absolute minimum. I say this only because we all need to learn from our mistakes - lord knows I still butcher hands all the time - but your mistakes are costing you sooooo much money. Think of all the value you're leaving on the table.

In the QQ hand - what hand did you think villain was checking on the river that beat you? Checking that river is atrocious, especially when you say villain was a station. You think she's folding to a small bet on the river with top pair?

What hand did you think villain had in the flopped straight hand that beats you when he checks after the board pairs and you check to him? Why would villain suddenly bluff the river after you called his flop raise and he checked the turn? His line makes no sense and he knows he's getting called.

If you're going to check call, just bet. Don't wait for opponents to bet for you. And if you're beat, they will almost always tell you.

If you 3! flop and V called and board paired, I'm still betting for value and may well just ship it because I think I can still get called by worse - remember, more draws than sets in terms of combinatorics, and I still think sets raise more on the flop. Especially if I don't think villain will bluff his missed draws.

At first I was thinking that, too. Then I wondered if there are a lot of Vs who will flat a set in response to a 3b. From his perspective, would a 4b shove fold out all the stubborn AA/KK in my own range that he could just wait to get value from on the turn? Or does he think I'm committed once I make that 3b? If we use 25% as the borderline for commitment, $185 out of $450 puts me at 40%, so by that standard I'm way over the line. I know a shove from him is also the best play with a set if I ever do this with AKdd.

If villain has a set he will probably fold to a diamond and possibly a 4 or 6. Good chance he thinks you have an overpair...make it $130 total to go (includes your $25), ship turn.

One other point of clarification: If I 3b $185 and get called, AND I'm planning to shove $251 into $417 for literally any turn, is there any merit to simply shoving dark before the turn in this particular scenario?

Never shove dark

I'm not talking about making it into any sort of habit. But in this particular instance, is there a chance it might cause villain to level himself into making a call he wouldn't normally make? Can it cause my hand/play to look a lot more desperate than it actually is?

No only makes you look strong(er)

If you dont want to 3bet this flop (which is probably pretty bad unless youre a real nit) then flatting flop and lead/shoving turn is a good line to take.

So... What happened