Hi, if I am not wrong, you have to talk to him after playing or skipping RPG during the weekend nights (Thursdays included)
EDIT: Go to the kiosk and talk to 'Santa' about idols in different days.
Eventually, he will provide you Kaoru's DVDs and a DVD player.
By watching the DVD, Chloe finds out that Kaoru is 32. Now I am stuck there, not knowing how to continue because talking to her on the basement after playing the RPG game nothing changes.
Full DVD solution:
1- Play RPG till full friendship (7, 7, 6)
2- Talk with nerds about Kaoru age
3- Drive by scooter to kiosk and talk with santa till he find porn magasine with OUR Kaouru (may take different days)
4- Buy DVD no. 1
5- Back to home, on desk on the right from laptop got new option but no device to watch "ancient technology". Back to santa, buy DVD player, back home and watch dvd no. 1
6- Get back to kiosk and buy DVD no. 2, buck to home, watch it
7- Back to santa, bay DVD no. 3, 4 and 5.
8- Back to home, watch them...
9- Go to Pizza Girl (no Walmart), start delivering pizza and go to Players apartment (other part of map). play with them (can slut-chit) and there be new option to chose reward, go to the desk and get new magazine with DVD. back to home and watch.
That's it