My friend likes to bet like 1/2 pot bets to "see where he's at" and then fold to re-raises if he thinks he is beat and i can't seem to persuade him otherwise (like when i think i'm priced in to the call). We talk quite a lot of poker and he is pretty conservative whereas i like to make plays and am not that afraid to get my money in.
It's good to have another perspective and these are some hands he didn't agree with me on:

However these are a couple of hands that perhaps i could've played better and i would like to know your feedback on them people.

Hand #1

Party Poker, $0.10/$0.25 NL Hold'em Cash Game, 6 Players
LeggoPoker.com - Hand History Converter

BB: $25.33
UTG: $30.79
MP: $30.66
Hero (CO): $35.52
BTN: $23.95
SB: $7.04

Pre-Flop: J J dealt to Hero (CO)
UTG calls $0.25, MP folds, Hero raises to $1.25, 3 folds, UTG calls $1

Flop: ($2.85) 5 6 8 (2 Players)
UTG checks, Hero bets $2.71, UTG raises to $5.42, Hero raises to $13, UTG calls $7.58

Turn: ($28.85) 3 (2 Players)
UTG checks, Hero bets $21.27 and is All-In, UTG calls $16.54 and is All-In

River: ($61.93) 6 (2 Players - 1 is All-In)

Results: $61.93 Pot ($3 Rake)

Villain was 60/4/0 over ~ 30 hand sample and had history when he limp-reraised from UTG and i folded JJ on a 6 99 flop to a check/raise.

My thinking is board is draw heavy and he could have a combo draw that just called flop hoping to hit it. Turn missed OESD and flush draw so i decide to put him all in incase he was chasing.

Hand #2

This hand was a fun hand, villain was relatively unknown at the table but playing a bit tight over ~20 hands. He'd stolen my blinds for last 2 orbits.

Party Poker, $0.10/$0.25 NL Hold'em Cash Game, 5 Players
LeggoPoker.com - Hand History Converter

UTG: $14.71
CO: $25
BTN: $25.99
Hero (SB): $25.10
BB: $35.23

Pre-Flop: Q K dealt to Hero (SB)
2 folds, BTN raises to $1.25, Hero raises to $3, BB folds, BTN calls $1.75

Flop: ($6.25) 4 J 5 (2 Players)
Hero checks, BTN checks

Turn: ($6.25) 7 (2 Players)
Hero bets $5.94, BTN calls $5.94

River: ($18.13) J (2 Players)
Hero bets $16.16 and is All-In, BTN calls $16.16

Results: $50.45 Pot ($2 Rake)

Will post more after i finish completely. Playing and posting probably a bad idea

Clar

*edited out results since they shouldn't matter right?*
*edited #2 because my title was dumb and i was slightly tiltish at the time*