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Dean's never been one for monogamous relationships. He thinks they're a curse for hunters. You finally get close and open yourself to someone and then something happens where it bites you in the ass. Either a supernatural reason or one of you can't take it anymore. He's seen what happens with hunters who've been in love. His dad lost his wife to a demon and burned on the bedroom ceiling; Sam lost the love of his life the same way. Ben and Lisa were almost tortured and killed from having been around him, so he had their memories of him and the hunting world removed. No one was safe around hunters.
Dean would rather have his one-night stands. A little night of fun and then gone to the next destination. No worries of demons or the rest of the supernatural horde coming after them. A woman once asked him why he didn't do relationships. "Blame it on my wild heart, sweetheart. Why settle for one when there are so many options to choose from?"
That was his motto and he followed it like a religious zealot. Until he met you. A beautiful, badass hunter, who made beheading vampires look like a sexy pole dance. You caught his attention from the start and he knew his one rule of not getting seriously involved with anyone began crumbling.
Now staring at the little black box in his hand three years later, he feels there was a reason he had that rule and that no other relationship had worked out.
He had been waiting for you.