Next event step has dependency on opportunities that you don't have unlocked. Put spider in Alice bed at night when she is alone. After several advanced spider killing sessions Max can invite Lisa to watch how those crawly things should be killed.
Events leading to Ann's new job in your picture depend on interactions between Max, Alice and Lisa and then other set of events with Max, Lisa and Ann. Spoilers.....
You must not be on Olivia-girlfriend path in your game. Can't tell if you are in correct path based on your screenshot. Although Hot Coffee opportunity would indicate that you managed to unlock town with Lisa and it should not be possible with Olivia as Max's girlfriend.
I suspect you haven't finished talks with Lisa at 15:00 near school as it should unlock one more opportunity some time after hot coffee.