Found a bug. Not entirely sure what cause it but here is what happened:
After my night-out with Angelina, when I stepped out of her apartment building, I was caught and stuck in a loop of being informed about having Mammons powers, phone ringing, Leslie saying one word, then the info came back, the phone rang, Leslie said one word, etc.
When this happened, I was still on good terms with Leslie (She had not yet gotten mad at me). Also, I had not waited 2 days after ordering the dress for Angelina, I went back the following day without the game telling me.
So my guess is that there is a missing or faulty switch, should be fixed easily.