So think about your thought process for a moment. Imagine you were cheating and could see his cards. You say you feel his donk was weak. Why raise him? Do you expect a player to call with a weak hand? Remember, in poker your goal is to make your opponent make mistakes. What is the best way for him to play poorly in this scenario? If we think he's weak then we want to keep him in the hand. Sure he might have some good equity, but we dont always know this so we have to consider our own mistakes too. Does 5betting with TPTK and drawing nearly dead outweigh him bluffing? I say no. While it might look like he made the mistake here I disagree, I think he actually played it kinda well. He'd get me to fold, and I crush these games for like 20/100 BB winrates.

Your goal is to always misdirect. You dont want your opponent to make the correct decision, you want him to make a mistake. By raising him you are giving him the opportunity to play correctly and escape his hand. I think the instances where you might raise TP only incur a 2bet, not a 3bet scenario. Lets say he donks outs from the SB and then you raise him, that has tons of merit. But he x/r putting you into a 3bet position, that I dont like.

Do not be afraid to get bluffed. Trust me you are getting bluffed constantly and you dont even know it. Probably for lots of small pots but sometimes a few medium one's which is all this would have been had you let it go. And I'm by no means saying you should go around folding constantly. I have a live vpip around 30% which means I'm pretty loose. I dont fold much as the aggressor, but a lot of times I'm only up against 50-100BB stacks so it's easy for me to be sticky and just hammer away with my equity vs their draws.

I dont think the way you played it was horrible. You had a slight read and were right. Lets pretend you folded like me and took a note, guess what; I'm 100% getting it in with him if this scenario repeats itself now that I know for sure how he plays. Maybe you felt a lot more confident in his playstyle than I do right now. All I have to go on is an anecdotal "he straddled and donkbet once" line. But there could have been a lot of nuances you were subliminally picking up on. He was drinking, he had a buddy at the table, he was a funny guy, wearing a tropical shirt, nice watch, wearing slacks straight from the office, flirting with waitresses, taking beats with a smile, you saw his wallet bursting at the seams with 100's, he had a BMW keyfob, etc etc etc. As played you had to get it in. Going forward the decision to gamble with him was still probably a bit spewy, now that you know him in and out you can confidently play for stacks with him at nearly any size.

Thanks for the detailed reply, this is helpful.

This is very accurate. I'm finding that I take too many high-variance lines. Sometimes it works out for me, sometimes it does not. What I'd like is for my wins to be more consistent.

I'm not afraid of getting bluffed in small pots, I hate the idea of getting bluffed in large pots. This led me to station-y over calling in my session tonight. But I didn't realize that was the problem till you drew attention to it here. Now I know what to work on. Its kind of a tilt problem. I'm going to work with Jared Tendler's books for study this week.

Looking back, I think I read boredom/frustration. He was trying to make a hand happen. He looked agitated instead of calm.

As for the rest, these are good reminders. I would want to keep this V in wide, not narrow his range to hands that beat a good Ace (or a random spew). And you're right, a 2bet is much better than a 3. That makes sense to me.