I just, with the next update, want to get past the whole party thing already. Being on Ashley's route, she's so concerned about the MC's involvement with Jenny that she's holding back advancing the relationship.
Yes the party is going to be a super shit-storm, mainly for Jenny, and I really do hope she doesn't want the MC to "work" for her afterwards. I really do hope Jenny's issues don't keep the MC away from Ashley (or whoever players pick for their LI).
I think, in my opinion, letting Jenny pay for the suit will allow the MC to buy Ashley a guitar, or maybe do something romantic for her to show how much he loves her. Jenny's going to get ambushed at the party but that's her problem. I don't want her problems hindering my MC keeping him away from Ashley.