treating women like a game
Sounds like he's still playing. 
The only reason I've wanted to appear not bothered is because he's described in the past that previous gf's have been jealous and bitchy and he sees me as different, thats its one of the many positive things about me. His previous gf's for e.g. would have balked at him spending time with other female friends which I don't, even if some of them were once sexual partners. I don't view any of them as a threat. So I'm trying to be perfect gf, in other words.
Sorry, but that is a MASSIVE red flag.
He has deliberately set you up to be the "cool" girlfriend who isn't like all the other crazy bitches he was with in the past.
You feel special not because he values you more or loves you more but because he tells you that you are superior to other women because you are not "jealous and bitchy" like them.
Except, he's bitch and you're jealous.
And it's no fucking accident either.
This is a relationship where you are being played and the prize dangled before your eyes is that you can be the girl to finally catch the player 
But in order to do that you have to squash down your own feelings and tell yourself that you are unreasonable and jealous but that you mustn't feel those things NOT LIKE THOSE OTHER WOMEN.
Stop competing with these women in your head.
That's what he wants.
I'd bet money that you're not the first whose heard all these lines about how you are different and cool and would never expect him to treat you nicely.