lol my goal (at least first play) is to somehow get everyone to sleep with everyone.
Though I tried second time and it seems like if you mess up one thing with Alison the sex wont trigger, you can reject Holly and go to lunch with her, and then reject Holly + Lena again and go to dinner with her and she'll still be banging Jeremy, heck you can even pass up Emma at the club and still no sex for you.
Also I did all the Louise friendship points and somehow she didnt even get into the argument with Ivy at the club? Do I have to take the point loss and tell Louise whats going on and "butt in"?
Also how to do Alison's friend?
For Alison, I rejected Alison for her lunch date and went with Holly, and also went with Cherry at the club. despite that, you can still have sex with Alison when she invites you out for dinner on Wednesday (iirc) but you need a will point. but you are right as far as banging Jeremy is concerned as Alison would have had sex with him once that way.
For Louise, you need to have a good relationship point with her as mentioned above and yes you have to tell Louise about Jeremy hitting on Ivy in Chapter 4. Pretty sure theres some stat requirement but I cant remember.
For Cherry, this was answered already in this thread. obviously you need to order the martini and show interest in her but you also need a stat requirement, think it was wit or something.
For Emma, again you need to have a good relationship with Alison that way you can have sex with Alison after passing Emma up in Chapter 5. I was able to do this despite banging Alison only once not twice in my playthrough.
Sorry that I dont know the stat numbers as I did not use any walkthrough when I played. I just experimented a lot and eventually got every scene. Hope this helps.