Putting yourself in the same place to get hurt all over again is stupid. The points you get for the leap of faith go hand in hand with the stupid points for taking that leap.
No two human loves are the same either, Castiel. It probably even works the same for all the types of non-humans in this world too. You'll never find again what you had with her, but it doesn't mean there isn't another love out there of a different kind.
Okay, I wasn't thinking about it like that, ew. Even the angels from really alternate dimensions that you've never heard of and they've never heard of you? And double ew, by that argument, all humans are brothers and sisters too.