I played a live game of 10c/20c NL w/5 people. Got into an interesting hand with my best friend.
All other players are fish, my best friend is a very aggressive player but no theoretical foundation with poker, just plays with a good feel for the game. He's a little too loose, and seems to have pretty elastic ranges based on bet sizes.
Preflop:
Straddle to 40c
Villain (Double Straddle to 80c) ~175 BB $35
Folded to me
Hero (But) ~175 BB $35 has AsTh

Hero raises to $2.20 from BUT, fold, fold, fold
Villain calls $1.40

Flop ($3.70) 8c7c9s

Villain checks, hero bets $3.60, villain raises to $7.80. Hero calls $4.20

Turn ($19.30) 9s

Villain bets $6

I tanked for quite awhile, obviously. My thoughts are his range is very weak here. He overcalls PPs, so I think he can have all of them, but I would discount AA, KK, QQ due to no 3bet, but I've seen him flat them before.
He is too loose w/Broadway, suited and unsuited. I think he calls pre something like 22+, JTs, QJs+, ATs+ (maybe A9s+), QJo+, ATo+. I'm not sure if he calls w/JTo but he does overvalue that hand sometimes, so maybe, but I feel like he would fold it to that big pre (he doesn't think about bet size relative to pot very much).

I don't like calling much, because 3 to a flush is out so we don't feel good about a Jc or 6c and I expect he will fire on a lot of rivers because of me tanking he might see it as weakness.
I was really debating raising. He bet $6 into $19.30 (maybe the biggest bet he made all night, he doesn't think about pot size enough) and both of us have about $25 behind. I would have to raise to at least $14 or more to get folds, but that would only leave $11 behind so I think shove is better but not sure.
My thoughts are his preflop calling range can't hit a lot of 9s or straights but because I raised I can have more nutted combos than him so I think I have enough range advantage to generate enough folds to shove for $25 into $25.30.

What do you guys think?

Since this is live, it's different than online. I think the thing is, you said that was the biggest bet he made all night and he doesn't take pot size and other things into consideration.

His preflop range makes sense, but when he raises on the flop what is doing that with? you have a 10, so you block out some of his straights, however you have no blockers to the clubs.

If you're friend is an aggressive player there are probably better spots, and rebluffing (if he is indeed bluffing) just seems unnecessary here. I think flop you should check back, and AP turn is a fold.

Thanks for the response. This was my train of thought as well, what can he really raise with. The thing is though, he gets very sticky in big pots, especially when raised preflop against me because I used to bluff him way too much. Thinking about it after the hand, I think he basically does this with all flushdraws, all straight draws, any pair, overpairs, and strong Broadways. He thinks I'm cbetting too wide because he checked. I also think I can get folds from overpairs and weak pairs because he tends to fold to big bets like this. It's tough because a lot of the dynamics are from our history.

Right definitely, but at that point you just need to make an adjustment. Low stakes players dont make as many in game adjustments and especially if this guy gets sticky in big pots because you've bluffed him before, rebluffing him is the worst thing to do EV wise. I mean, it could potentially be +EV in this spot (although i doubt it is), but you're basically just asking for lots of unnecessary variance.

I had a guy live tell me "I know you have junk, but the problem is..is my junk better than your junk?" In this case, I would say no.

But in general and going forward, just tighten up your game let him get sticky when you have decent equity and allow him to value own himself. If you had the Ace of clubs i'd be more inclined...but I think there are sooo many better spots for you to stack him. If you know he's making an adjustment to you because your super bluffy, then readjust and exploit him.

Also, even though your shove can fold out a lot of better hands..his flop raising range basically has you crushed and the turn only makes it stronger.

Another much easier way to exploit your friend would be to call him down with mid pair on dry boards. I think you're thinking about things the right way, but you're choosing poor spots.

Thanks! Awesome reply. This is almost certainly right. I ultimately folded because of that as well, thinking okay we can just get him with value. I've switched to mostly value bets against him a while ago, but he hasn't really adjusted much as I get a fair number of calldown from him when he has top or even 2nd pair and I've fired 3 big barrels for value.
Now, I'm really trying not to be results oriented with this, but what are your thoughts that about this: He showed me AhQd after I folded. Does this indicate that his c/r range on the flop has enough overcard/bluff hands to make this a good rebluff from me. I think he is likely to fire twice on that turn thinking i'll be scared of straight, flush, and 9s with these hands and putting these in his range really skews it towards overcards, overpairs, and weak pairs.
I know I'm already exploiting him but I hate having to just have a hand to beat him and wondered if I can get some more EV in spots like this. Probaby too risky though. Thoughts?

BTW, checkback on the flop does seem much better as I know he is likely to get sticky. Just didn't expect reraise and I really was trying to avoid a tough spot on the turn when he sees me check, but that was probably an emotional decision thinking back.

I think you and I play really similar but I'm trying to get out of that mindset.

Even though we saw his hand, what you should do is adjust your whole range.

This is my take on it, you're perceived range on the button is most likely 10s+, A10+. So you have high cards, and over pairs. The flop is connected and all low cards (now ask yourself if he is going to c/r you on a KQJ board), so he checks and you c-bet (but you c-bet too wide and he notices this) so he raises you because he thinks you're weak, and there's also a solid chance he's on a draw. Turn is not a good card for us, he makes a 1/3 PSB but you have very little equity and are either in a way ahead or way behind situation.

When he shows you his hand, he didn't really bluff you as he technically has the best hand...

If you want to get into more spots like this to beat him, construct a 3 bet bluff range (76s, other suited connectors, maybe even suited one gappers). That way, when you 3 bet you are balanced enough to hit flops with low and high cards (and since you have position, when he decides to bluff you...you take all his money).

When youre bluffing, you need to not only take into account your range but your perceived range as well. Why is he bluffing you in the first place? Then adjust your actual range.

Also, look at his sizing. It looks like his sizing is based off the strength of his hand, so that might be something you can exploit as well. My response is more to encourage the way you should think about the game and the in game adjustments you can make based off of reads.

Great analysis. I agree he just thinks I miss this board too much.
This is an excellent point about the 3bets. I've have really been wanting to incorporate light 3bets against him because he does raise a bit wide and tries to iso the fish. The problem is that the games we play at, the fish are stations enough to call my 3bets with crap and he also seems to be very unwilling to fold to a 3bet. Do you think the extra balance with the low SCs will make up for this if he is calling a lot of my 3bets.
Side note: I did get one squeeze through against his MP open w/CO caller. I had AQo, but I digress.

It just depends on his range and the fish vs yours.

If you 3 bet bluff just your friend (no one else in the pot), he either folds (making the bluff successful) or when the flop comes high cards gives you too much credit and folds to a cbet, or tries to outplay you on the flop when you're ahead, so 3 bet bluffing can make you less exploitable.

Now if a fish is in the pot, he raises to iso the fish (who is a calling station), you should never 3 bet bluff here because like you said the fish will call with random crap, and your friend is unwilling to fold. So in order to exploit this, you 3 bet your value hands but use a larger sizing because 1 or both will call. Then play post flop.

You never bluff a station, and it looks like when fish are involved and you 3 bet, your friend becomes stationy...so exploit that. If he raises to a dollar, make it 4 dollars.

Thanks again for the thoughtful responses I really appreciate it. I agree that to exploit the fish I need to be value 3betting, which of course I do. I think that we also need a wider value range against them and I've been unsure how wide to make it. Just as a point of reference, can I go to like A9s, A5s, K9s? I've been playing around with that one a fair amount.

I widen up based on specific tendencies. If i see that villain will over play A4o, then yeah A9 crushes him so totally.

If they are extremely nitty, then I play basically ATC, two barrel and take down the pot and fold to any aggression (they are folding a ton when they don't hit, so bluff them more)

The question isn't whether or not they are a fish and what hands you should play, but what makes them a fish and what lines/hands can you take to exploit them whether it's calling too much, folding too much, bluffing too much etc.

Thanks man. Great responses. That game I ended up well ahead because I started really getting the fish by cbet/barreling turns more when I saw the call flop/ fold turn line a bunch. That's something I wasn't doing enough because they just seemed so stationy I didn't expect 2 barrels to be so effective. I will definitely try and look for some more specific adjustments per your advice.

I would c/b this otf as a default, I play online though

C/b as in check back or as in cbet? Thanks for the reply. I play mostly online as well so i think about the game that way mostly.

You can say "lol pot odds" in this spot and probably not have it be horrendous. I assume that turn is meant to be 9c not a second 9s.

Bad live players tend to bet small on scare cards when they have something weak but made. They do it sometimes when they have something nutted too and are making the "please don't fold" bet. So this sizing is more polarised live than it should be but it tends towards a bunch of made hands against which we don't do very well. You can be dead here to boats, or flushes that don't like the paired board, or drawing to chops vs JT.

It can be airballs making spazzy bluffs but those tend to bomb. Make a mental note of these spots because it's probably a huge sizing tell.

Yeah definitely 9c on the turn. Lol

check back otf, this a good candidate to put it in our check back range imo

Agreed. After looking at it after the hand, better to have in check back range. In the moment though I was like holy **** I actually have equity on this board?! Bet lolz. I also wasn't sure if he is good enough to realize how often my range misses this flop. Apparently so.....