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Bobby and Dean tell Sam everything about their 'first contact' with Castiel, angel of the Lord, of course. Which is why, much, much later, his baby brother will joke that it's no wonder it took Casdean a while to develop. (Dean doesn't know what is worse. The fact that they have fangirls out there, the fact that Sam can't even bother using the right fucking tag if he has to tease, or the horrifying suspicion that he does because of that 'list the top first' old understanding.) After all, Dean sent his angel awfully mixed messages.
Dean, every time, tells his brother to cut it out. What he really wants to say is that Sam is supposed to know better. After all, isn't Sam the one who's all empathic, always ready to talk feelings? The one who gets way too emotionally invested? (Half the time with monsters, but hey, Dean won't judge kinks if he's not judged.)
Then, why doesn't he understand that – Dean stabbing Cas, and his angel's smile, could have been a more perfect representation of love only if, instead of freezing (because uh-oh, the demon knife wasn't working, what was he supposed to do now?), he'd have both twisted the blade and teased Cas into snapping and using his angel blade on him. Isn't there a saying about love being the equivalent of giving someone a gun and trusting they won't shoot you with it? As much as he's comfortable with guns and rifles of all kinds, there's something more intimate in a knife. And the truth is - they do. Shoot you, carve you, take that chance to hurt you as deeply as they can.
They might not mean to. Most times, they don't. But it doesn't mean they won't. As someone who's done the hurting at least as often as he's found himself devastated, he knows that selfishness can be curbed. But when you're convinced you're acting in another's best interest, another you love. There's no stopping that, with force or begging. He's been lucky enough that, every time, he's had a second chance (third and fourth and so on). He's offered his number of them, too, because it turns out that even angels aren't perfect, and can mess up like the most human people.
Actually, maybe that's part of what attracted Cas to them. Team Free Will, sure. More Team Well-intentioned Screw-ups. At least, they realize that. Never seen a flash of doubt in any of the other winged assholes, no matter what awfulness they committed. It's hard, sure, but at least they have some chance of learning from their mistakes (even if, damn, established patterns of behavior are so hard to break, even when they hurt you and piss off everyone else). If you think you're above reproach, you'll never change; at which point the only way to deal with you is to kill you, and make sure you can't come back, no different from any other monster.
For all the mistakes, the hurt, and the chaos, there's one more obvious truth. Love is like Achille's spear (hey, he reads...just in an eclectic way). It will wound you, but it's also the only source that can heal the harm it has caused. Now, sure, his angel boyfriend is a cut above the rest in healing (maybe not above other angels, but definitely above anyone else Dean could have a chance with). But it's not grace that's needed to help him out, not when it counts. Which is good, because it means that Dean can repair the damage, when - as he has, and undoubtedly will - he unwittingly hurts Cas again.
That's when Cas pops in again. One look at him, and his angel asks, "What are you thinking about?"
"Us." He smiles, but it's not enough to erase what Cas must have read on his face.
"Something wrong?"
"Not now, no. And whenever we stumble - it won't be anything we can't get over, right?"
A few years ago, Cas would have said that he couldn't possibly know. Now, he replies, "If you'll be willing to, I have no doubt."
"Cas, I'm not - "
"The one who ever gives up, I know. It's part of what I've loved about you, all along. You should know I can be as stubborn as you are."
This time, Dean laughs, and it's honest. "We match, huh?"
"Let's double-check." The kiss is expected, and glorious.