"I don't think the school board will like that, but I'm willing to come with you there anytime.~"
— While Cheerilee likes to keep her private life away from her students, Discord has sometimes burst into the classroom at inconvenient times to present Cheerilee with gifts or plans only to be shooed out with a broom. Besides that, they have a pretty sweet and healthy relationship with lots of (safe) chaos reigning and kisses. This is a massive slap in the face for literally anyone she tells, that this collected caring school teacher is in kahoots with an interdimensional danger noodle. But really, he's such a fun and funny charmer who helps her get away from her quiet uneventful life. Let her live a little!
Discord, on the other hand, has always loved having a counterpart with a lot of spunk to give. Cheerilee is an impressive woman and he's heard her shout at those little demon students (how does she deal with them all day?) and put her hoof down. And, well, whenever Discord sees authority…he can't help but try and mess with it. This, unfortunately, turned into a lot more messing around in different ways than he intended, and they both ended up liking each other a lot more than he thought they would.
The person most affected by this….is Suave. Suave fucking hates Cheerilee and her dad being like this. And what she hates the most is they made her a little sibling, one that totally throws off half the plans she has for the world, but this is fine. She can fix this. Of course she can fix this.
Jasmine Leaf also hates that her sister is badunking with Discord, because well….as we all know, she initially did not have a great meeting with him.