THANK YOU SO MUCH FOR PLAYING!!! I am beyond flattered!!! There's so many amazing fan arts on tumblr and twitter and I never could have guessed something I made would have such a nice community!
I don't have a MAC myself so I can't probably test it or know how the files work, however, someone else had a similar problem so I made a small workaround!
To do it, at the very beginning of the game when the Bureau asks you questions, answer that you HAVE played the first game and that you CANNOT access the game files. And then after you've unlocked ALL the cross dates then go to the main screen where you can choose to "pick a boyfriend" and a mysterious phone call should happen.
If any of that doesn't work, please let me know, I might have forgot to make a MAC version of that workaround. I'm really happy with how the dates with Ashton turned out and I don't want anyone to miss it!