Teen aspiration drama lama

I would suggest that you Exit to Main Menu without saving and then reload the save. That way, you can do the breakup in person. 

I don't have phone breakups in my game, which includes High School Years, so they were probably either added later or added by a mod, and that's why they don't work. They weren't part of the game at the time HSY was released. 

I just ran into the exact same issue. I had to cheat the aspiration complete because it didn't count the break up over text interaction as a break up. I hope they fix that at some point, because it's a legit way to break up with a sim so it really should count.