You need to get at the blowjob stage of the Mentor quest. Just before it .... or just after the first BJ, I can't quite remember the timing, Ann will talk to Kira (and you'll listen, as we're talking about Dirty Max) and Kira will suggest either having a serious, if hidden, relationship with Max or ask him if he's OK with her allowing her boss (Eric) to seduce her or not. Max'll say he's not quite sure and later you can go talk to Ann and give her your results. I've chosen to let Ann allow Eric to seduce her and skipped some days and I still got nothing, not even an announcement at breakfast that Ann is seeing Eric.
Eh, as far as "NTR" (not really, since he had sex with "your mom" and you aren't supposed to do that with her) goes, it was ok. As far as character development, I don't think it was that bad. I mean, we all saw was a slimy, sleezy PoS he was without it taking a lot of time to do that. The conclusion was pretty good. I mean, I enjoyed getting Kate's mother to make him a sex slave or whatever she did....
Too bad we don't get any sex scenes (I'm not including the few porn videos/slideshows in there) in the Max storyline yet. We only get some blowjobs and that's it. And I'd rather see Max's part develop further, it's a much funnier story...I mean the way Max acts is just hilarious to me.