bennettxgemini:

I didn’t even know this was a ship 👀

I really don’t remember there interactions that much and kinda feel bad if Emily liked him back then cuz he was so UP Katherine’s ass.

I’m going to say I’m open to it and they would look cute together 🙂

Honestly the way I imagine the ship if it ever happened is Damon seeing through Katherine and taking a liking to Emily instead as I kinda set up here. And then Katherine not happy because she does not share her toys, least of all with her slave. To me that would be a lot more entertaining than the actual 1864 SL which is one of the more well done plots of TVD but kinda falls flat to me. Like when you find out the full story it’s kinda lackluster to me–I expected more from it and this was one of those headcanons I had early one and still kinda wish it had happened, but there’s a lot had happened.