Relatively new 1/2 NL. Hero starts hand with ~360, in for 400. Villain has 1k and is drunk, talkative and friendly.

Before the hand even starts villain puts 16 on the button for a straddle. Dealer tells him (and the table) it's only a $5 straddle and he can't make it for more. Player warns table that a raise to $16 is coming.

Two limpers already to me in MP and I wake up to AsKd. I decide to limp knowing a raise is likely coming.

Another call before villain quickly checks hand and taps the $16 off the dealer button and onto the felt.

First limper (old asian lady) calls w/out hesitation. Second limper (tight asian male) also calls. These guys definitely have better-than-decent hands. I get the feeling that BTN will defend his raise no matter what I make it and I don't want to own myself with a c-bet on the flop. So I opt to call and see if I can hit the flop. We're four to the flop.

3dAh4h

Checked around to the villain who does the math out loud of how much is in the pot and then bets $45. Old lady folds, tight young guy folds.

I think about raising, even jamming him. For some reason I wanted to see a non-heart turn to help convince me to jam. So I call.

Turn is the Jh.

Check to the villain who fires $80. Seems like he's betting just enough to keep me around as the bets are 1/2 pot sized. I know he's talkative so I decide to talk.

"You like the Jack?" I ask.

Villain: "I like it a lot."

I think a little and decide I'm probably behind.

"If I fold will you show me your flush?" I ask.

Villain: "I usually never show but you seem like a nice guy and I'm just here to have fun, so sure."

That answer suggests I'm beat. Maybe not. But I fold.

He shows:

Lessons learned ...

I should have absolutely raised preflop, probably after his button raise but also potentially before (maybe I could have made it $16). The thought in my head at the time was "pop it to $65" and isolate. Not sure if that was enough. That would have also meant a flop c-bet of probably $110ish or a check-raise all-in depending on what the flop brought. I think raising the villain and then check-folding flop (in case of a QT2 flop or something that misses me) isn't a move I like to make. Thoughts?

I also need to work harder on coming up with plans for following streets. It's not that the villain here was unpredictable as much as what his bets represented. Help here would be appreciated.

I can't believe you'd ever not limp-raise here preflop. there are almost 30bb in the middle when the action gets back to you, so taking this pot down preflop would be a great result. I think it's a huge mistake to just call here preflop the second time. a QT2 flop isn't even that bad, you have 2 overs and a gutter, stop being so pessimistic . my limp-raising range (AT+,88+KJ+, something along those lines) would crush his range so I don't think you have to bet very big on the flop. Around half pot seems fine, could maybe go even smaller.

I'd also bet the flop. I'd only not bet the flop if I thought the guy was cbetting almost his entire range into 3 others and kept on bluffing a lot in which case I'd not fold the turn. so yeah I'd have played every street differently

If BTN will defend his raise no matter what you make it, why didn't you shove?

I'm only getting called by hands I'm either flipping with (QQ-) or crushed by (AA, KK). Not worth risking $340ish to win $53.

So now you're saying that he won't defend (with the vast majority of his range that's worse than QQ) his raise if you size your 3bet big enough.

Winning $53 the majority of the time is huuuuuuuuge. You're only crushed by AA/KK of which there are only 6 combos left. Shoving pre almost certainly shows a higher profit than just flatting and playing this hand 4 way. Also if the guy is drunk and up a lot there's a non zero chance he calls you with a hand you dominate preflop. You seem very risk averse which is going to hurt your bottom line a lot.

There were 2 other weak tight players in too so he could mean them for the QQ+

Yea the situation is perfect for a back raise though I'm not shoving probably.

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My eyes started bleeding when it says u called pre

Newsflash. Their ranges for calling raises are waaaaaaay wider than you assume.

AKo is miles ahead of those ranges. 3 bet pre. You got exactly what you wanted. There is absolutely no compulsion to cbet bad boards.

What is your definition of "hitting the flop"? I´d say this is pretty much a hit. Bet when you hit.

You underrepped your hand and made a very nitty fold and maybe feel retrospectively happy about it. Hand not played well on any street.

Grunch

The other villains had two chances to raise PF and just called both times, so the chances you're up against QQ+ go way down, and I think you should have put in a huge raise after the raise to 16 and two callers. If BTN is going to call a super high percentage of the time, that's a reason to raise. It's not a reason to call.

AK is also much harder to play against 3 people than it is to play against a drunk guy who straddled.

Huh? That is inconsistent with what you said earlier:

So which one is it? Is he only calling with better or is he calling with a bunch of hands if you shove? Now you think he even folds AQ?

I literally gagged a little when I read that you didn't reraise PF.

Button range: ATC

Caller's ranges: capped at QQ and wide

You know the callers cannot ever have AA/KK here right?

It might be lazy but I would just shove here, expecting the callers to fold almost 100% of the time, and the button to fold his crap but call alot with hands we beat (TJ) hands we crush (AJ, AXsoooted) and hands we flip against (any PP). He's drunk: he calls us way often enough to make this a really profitable move. If he has AA/KK so be it, we made a good gamble. Our strategy against drunk gamblers must be to gamble along with them. We just fix the odds a little in our favor. And honestly gambling like this with drunk, nice people can be fun. If he wins say nice hand and maybe this hand starts a really good table dynamic.

The rest of the hand is meh, and I really wish you wouldn't post results in the op. That ended any good discussion we could've had before it began. But that's okay because I just can't get past the preflop play anyway.

You plan preflop worked perfectly... and then you decided to flat the $16.

The button is essentially raising blind, we have some dead money trapped in between with hands that are capped at medium strength, and we ourselves have a really awesome hand. Absolutely no reason why we're not 3betting big here preflop.

OK it's clear I missed my spot preflop. I won't do it again. I won't. I'm working on becoming less risk averse. This is a step in the right direction.

Do you think a raise to $65 would have been enough to isolate? If so, what's my play if the flop is not A or K high vs. drunk's ATC?

Raise pre for value and lead flop for 2/3 pot. As played its not surprising I folded due to the passive way I played the hand. Don't rely on someone being honest in poker, bet your hand.