Dean swore that he would be a hunter until he died. Well, he didn't have much of a say. Once you're in the business, it's kind of hard to leave... A special thanks to John Winchester for dragging him (and Sam) into it when they were children! A+ parenting, really.
Anyways.
Then he met you. Sweet, gorgeous, adoring you.
You challenged his entire look on everything. Meeting you on a random vamp hunt back in '09 really did change him. He never believed in true love at first sight, but there you were.
And you had been together ever since.
Cut to a visit to Garth and Bess, prompted by a certain enthusiastic werewolf telling Dean that he needed to come visit him and his family.
That's where he got the bug. Seeing Gertie, baby Sam, baby Castiel... It sparked something in him. It made him want out of the life, and to start an apple pie life.
...So, that's why after you two were settled in bed, on the verge of sleep, he blurted out, "What would you think about having kids?"