Return of the meme

Because I feel like I haven't been doing enough memes of late, I', going to start digging through them and bringing them back...at least until I decide not to again.

Give me a pairing and I'll tell you:
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: