Both of the first match make for some of the saddest writings of the strip, so it is a tricky one for me to pick. I think I might be like the MitD here, but I do find Tsukiko's death tragic and will vote for Redcloak & Tsukiko.

The second one is a matchup I'm less torn up about, although I'll admit it's still not an easy choice. I think I'll lean towards Elan & Julio just because they're a funny pairing.