Screw the Timeline, they would've been so good for each other.

Azazel and Dick Roman (Azoman) would've made such a good couple (even if they destroy the world while they're at it). Like Dick is calm and calculated and would give Azazel that balance that he needs. Meanwhile, Azazel will make it his mission to not only seduce the Alpha Leviathan but also add some spice into his life (shall we say). And I think it would be cute AF. Dick would, honestly, despite certain obvious facts, would make such a perfect step-dad to Meg and Tom. Of course, he would be the calm parent that they could talk to about relationship problems or being mad at their biological father or whatever else might be bothering them. And he'd be very, very protective of them. So, protective, in fact, that he would make Azazel look nice which is saying something. Both of them (and the Masters') could've benefited from having one another but, of course, when the one was alive, the other was in Purgatory. So, that sucks.