Put a pairing in my askbox and I’ll tell you the following:

pinkie-pi:

1. When or if I started shipping them:
2. What I think their challenge is:
3. What makes me happy about them:
4. What makes me sad about them:
5. What moment I wish had never happened:
6. Who I’d be comfortable them ending up with, if not each other:
7. My happily ever after for them: