Was in a small tournament with a couple of regs and a dude who clearly never played poker seriously in his life(was constantly donk-betting, limping with premiums etc). He still sun ran with multiple KK, AA, AK limp calls and knocked out a much better player who shoved AJ on the button by waking up with AQ in the big blind.

Now HU with him, I have about ~30bb and he has ~25bb. I still don't have a good idea of his playing style bc the only hands that he played that went to showdown were absolute premiums(sets, AA, straights, etc) so he got a lot of respect at the table.

I wake up with A2s in the big blind. He limps, and I raise to 2.5bb, and get called. Board comes A53, I bet 2bb, he raises to 5bb, I call. The turn comes a 9 and the river comes a 3. I check it through and he checks it back. He shows Q5 for mid-pair and I win.

Now I become unsure if he just overvalues any pairs on high card boards.

After losing a few hands(he constantly raises insanely large on the button(5bb) and bc there is an ante I was bleeding out quickly). I get JT on the button. I raise to 2.5bb and he calls. Board comes QJ3 rainbow, and he picks up a few chips as if he wants to donk-bet, but then puts it back down. I was kind of irked by that, but I bet out 2bb, hitting middle pair on a relatively dry board. He then check-raises me, large to 7bb. I block most of his semi-bluffs(T9, KT--although I'm not sure if he will check-raise open-enders in the first place). I fold, and he shows me 35 for bottom pair.

The next hand, I get pocket TT. He limps, and I raise to 3.5bb in the big blind. He calls, and the flop comes K53. Tbh, I wasn't feeling super comfortable playing with him OOP and betting on a K high board in case he check-raises me, so I checked the flop(mistake?), and he checked it back. The turn comes a Q, putting 3 diamonds on the board as well as two over cards. He then overbets, effectively putting me all-in. I fold.

I bust out the next hand by getting A8s in the big blind, shoving, and getting called by AA. Felt so stinky with the angling and how I misplayed a lot of these hands.

So I guess my question is three-way:
should I have squeezed out extra value OOP with A2s in the first hand on the river?
should I have folded JT in the second hand?
should I have bet the flop with TT?

Thanks!

If he is loose i think you could raise the TT hand a bit more pre and also bet flop.

I was considering shoving TT, and retrospectively I think I should have. I had no reason to think he was loose as all the hands he showed at showdown was AT+(he was getting absolutely hammered by the deck), but the Q5 and 35 hand surprised me.

Its important to say how many blinds each of you has before each of the hands. When I have < 15 blinds I will just jam pre-flop so with TT it takes away all of the post flop nonsense here.

It is hard to evaluate how to play the hands because we have the results. It is clear though that Villain is c/r or raising with bottom pair but it isn't clear if you had seen him do it with top pair. Ironically he may have been just calling with top pair to get you to bluff 3 streets.

If you had bet the turn with A2s on the first hand I doubt Villain would have called. Typically when I am raised on the flop I don't bet the turn because I think it is very possible I will get raised again. I think you were correct to check the river and allow villain to bluff (which he didn't). If you bet and he raises you would have to fold because of the 3 on the river.

With JT and a QJ3 flop I would typically bet 66% pot because the range favors the pre-flop raiser. It turns out that when people pick up chips to bet and then don't bet it is a tell that they are weak with a draw of some kind (or in this case bottom pair) and don't want to have to call. Or on the river it can mean that they have a bluff catcher and don't want to have to call. This is a tough spot once Villain c/r's and you do block some of the draws. But given Villain's history of overbluffing it might be the perfect time to call and see what happens next.

With TT I would cbet the K53 flop HU regardless of what Villain does. If villain c/r'd the flop cbet its a tough call but I would call (or shove) based on all of the past raising. My guess is that villain's raise may have been close to or more than 1/3 of the effective stack which for me is time to jam. I had a similar hand here in Prague where I raised with TT flop came Q98 possible flush draw I cbet and villain c/r'd which he did repeatedly. In this case it was for about 40% of my remaining chips. So I jammed and he called with J9 (and I ended up winning). It was in the middle of the tournament but we were HU in the hand. I mention this hand because when I see people overbluffing its important to take control of the aggression.

Doesn't it make sense to check our marginal hands and bet more polar, top pair+ and maybe things we are more okay folding?

I like to mix in limping HU when I think I have a skill edge against a spewy splashy player. It protects you from preflop allins esp at this stack depth and allows you to play defensively and realize your skill edge on later streets.

The JT hand on QJ3, I guess I check this a lot vs this player. All of the over card turns favor you and you block the OESD that he check raises with here (9T and KT) that you’re ahead of. His pp’s call a cbet here but they also jam preflop a lot so I don’t think there’s that many here. He calls with worse jacks and calls (and sometimes raises) his Qx and better. He can call/raise/fold his 3x here. I think you make a lot of money by checking here and calling his turn stabs and his river spazzes. You don’t want to be in the blender vs bad players esp when you have a solid hand on this flop and he has a high check raising frequency. You will still get value from Jx on later streets and you give him a chance to blast off with air. And ofc to be results oriented, you avoid folding better hands to his c/r.

Thanks for all the suggestions; I think I like checking with JT here too--I feel more comfortable calling his turn and river bets as well, esp since it's likely that my hand/range improves on later streets compared to his.

BTW, I did not have any information regarding the specific nature of the hands during the HU play other than the Q5 hand which went to showdown. He told me he had 53s for the QJ3 hand and also Qx with a diamond(although he did flash me a Q after I folded) in the TT hand after he won the match with AA, so I didn't have the information that he would be as creative(?) as raising with bottom pair. Infuriating part was he said he thought he was raising the 35s hand for value against my Ax nothings, so...idk what to make of that. I don't think he was lying and he found it funny that I folded a J.