You were a hunter who had to give up the life after you were young, stupid and got married at the age of twenty. You’d waited a while (six years, to be exact) before having a kid with your then husband - now your ex - but that one kid became two, and then three. And then your husband up and left. Bobby realised you were struggling and sent over Sam and Dean to help, as it was hard with three young kids, one of which was a baby. This time, they came with reinforcements in the form of Jody Mills, and her and Sam took the kids for a day out and left Dean to help you relax.
“Hope you’re feelin’ better, sweetheart.” Dean smiled softly, giving you a warm mug of hot chocolate he made to relax you. “M’ guessin’ the squirts are a handful when we ain’t here.” Secretly, he thought your ex was an asshole for leaving you. He looked you over and you were a damn catch.
Dean reached forward, tucking a loose strand of your hair - that didn’t make it into your messy bun - behind your ear. He didn’t like seeing you this tuckered in the slightest, and knew that life without your ex must have done a number.
Then he offered you a suave chuckle, trying his best to give you a shoulder. Or comfort. Whatever you needed. “Good thing that Sammy, Jody and I swung by, eh? Else you’d be workin’ to the bone.” You were extremely fond of Dean and his Dean-ness, and Dean had the softest spot ever for you and your kids.
You were a damn good hunter back before you quit. You’d gotten out of the life, but Dean felt upset that you’d been thrown into something equally as taxing. Damn your ex-husband.