Villainous Valentine 'Achieve ex status with 5 other Sims' not working

I have a sim trying to complete the Villainous Valentine aspiration and while i've had no issues with the two other requirements, however the "Achieve "ex" status with 5 other Sims" will not work. My sim has ended relationships by being broken up with, deciding to just be friends, and initiating a divorce and none of these did anything for the aspiration? It still says 0/5, why is this happening?