#I know headcanons on this topic vary widely but IMO my favorite headcanon is that the two of them only ever fell for one (1) human each

[charlesemersonwinchesteriii]

for the not dating thing, aziraphale & crowley (gomens or spn take ur pick :))

Do you know, Ana, I think you're the only one here who can actually remember my ancient crush on SPN Crowley from all those years ago. 'Twas truly as if a demon possessed me in those dark days. And as soon as I emerged from it I was baffled. What was all that about, I asked myself. How did this stupidly undeveloped antagonist with a bald spot and an accent have me so enthralled just because he had a little sobbing meltdown that one time, I wondered. Surely this will not happen again, I said.

Anyways there are so many clear reasons not to date Fergie here that it's an obvious no with the sole exception of ONLY if I got to take him and Castiel on a double (er, one and a half, I guess) date IMMEDIATELY after they both became human in 8x23, thus catapulting both of them into an actual meaningful character arc where their transformations stick for more than 3 episodes. If the Winchesters try to bother the three of us while I do this I'll fucking kill us all with a grenade btw. Anyways

Aziraphale & Crowley

I love them so much and it’d be so tempting (lmao) but unfortunately I just don’t think they’re ready to add a third to their relationship yet. Like they’re in a really good place right now but I think they’re gonna need at least another century to be up for that. Aziraphale contains foibles and eccentricities the way humans contain water, of course, so he’s never not a challenge. But I think probably the biggest issue would be that Crowley would be completely neurotic about the whole thing. He would ask you which of them you liked better secretly deep down and if you said “Aziraphale” he would turn into a snake and pout in a hole for a month straight and if you said anything else besides “Aziraphale” he’d be flabbergasted and offended. You don’t agree that Aziraphale is the bestest most important entity ever created in the entire universe??? Oh!! Oh!! Jail for you!!! Jail for you for Six Thousand Years!!!!!!

Also “OP what about dating just one of them on their own?” Are you out of your damn mind. Are you insane. Look me in the eyes. Do Not Separate Them.