I’ve played through trying to do Dans route a few times but for some reason everytime I just end up sleeping with him a lot and not actually getting to date him. Does anyone have any tips?? 

You probably just need to spend more time with him. Make sure you successfully visit Q&A at the first possible opportunity (September 9).

In addition, note that Dan likes it when you do sketchy things, so making some more... interesting decisions early on (like snooping on Adam's computer) will help establish your personality as someone that's willing to take more risks.