It is likely a scripted RP loss, since she likely is upset that Ashley brought the MC and not her and resents the MC as a result.
I wouldn't know about failing checks, i tend to edit the save file and max out the RP stat and just play normally, i am not much of hoping its the right choice, i would rather pick what makes sense to me for my character in an RP sense, i mean when i played a complete horn-dog route before episode 8 came out and it sounded like the MC is so clueless and dumb and when i was his age and lacked experience with women, i never acted like he is....its rather dumb. But when i focused on say Emily, the MC's personality seems more balanced, but ultimately still a whiney child.