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With the Highschool DLC NPC Relationship Autonomy Interactions were added which happen totally random, so i added some tests to hopefully fix that:
Ask to be Best Friend - Must be at least friends
Ask to Prom as Friends - Must be at least friends; No Romantic Relationship
Ask to Prom - Must have Romantic Relationship
Ask to be Boyfriend/Girlfriend - Must have Romantic Relationship but not Engaged, Married or Significant Other
Break Up With - Must have Romantic Relationship. Optional as Addon: Not Engaged or Married
Propose - Must have Romantic Relationship but not Engaged, Married
An Age Test has been added to all of them as well: Teens should only ask Teens, and Young Adult, Adult, Elder should only ask Young Adult, Adult, Elder