ugh terrible play by me

i figured if i had the best hand and pushed on him he'd fold (with his hand he wouldnt) or if he had a 5 or JJ hed just call and stack me. anybody some advice? i was trying to let him bluff if he just had a J or air but didnt wanna get stacked if behind.

i would check raise all in on the turn - definatley feels like AJ or KJ here

Something like 56 is possible, probably not A5 unless hes a dumbass. I think his raise on the flop was to see if you had an overpair or were continuation betting AK / AQ or a lower pair etc. So when you flat call and then check the turn you look weak and for this player he easily assumes he has the best hand at that point. Also some players might slowplay a 5 on that flop especially if they are pretty sure you have an overpair and no flush draw. On that flop I think people raise with AJ, 56 or maybe a draw to try and get you to fold. I would either re-raise on the flop or bet out the turn to get a better read on the guy (calling flop and betting out probably best). Basically you fucked up the turn the most I'd say, check/calling just looks really weak - you might as well bet out if you are going to commit more money to the pot because you get more information that way. Bet out something significant and if he pushes then you can probably lay it down.

Checkraising like Tom said could work too but its risky since he has Ad he might just take a free card. You definitely establish strength with a checkraise.