In a lot of ways, Gabriel is extremely human to the point of coming off as a cocky frat boy or an overgrown child. He speaks in pop culture references almost to the point of it being a second language, which puts him way ahead of most angels in that department. As evidenced by his decadent apartment in Tall Tales, he’s hedonistic to the core. Whatever he wants, he gets, one way or another, because he’s too relentless and stubborn to give up- it was only after Sam begged him and he'd gotten so bored with the failed outcome of his game that he let Sam go in Mystery Spot, for example, which strikes home as a rare occasion when his tricks haven't worked, given how aggravated he seemed by the outcome.
All of this, however, is part of his public persona, because it’s important that Gabriel keep his true feelings hidden and thus he does everything to avoid looking like he gives a damn until forced into the open. There's so much to him that it's almost impossible for one person to peel back the facades he puts up and that makes it hard for people to get close to him, due to the fact that he pretends to not care about anyone or anything and uses his sarcasm as a defense mechanism- Dean calls him on this in Hammer of the Gods, even noting it's something that they share (although, they have completely dissimilar reasons for sharing it- Gabriel uses his to maintain his standing as a dominant force). Getting past all of his defenses is something that just doesn't happen (except in rare cases), because anytime someone does, he slams the walls right back up again, although, by that time, he's probably already snapped and shown that he's affected and given himself away, anyway. He is extremely fond of denial and does not like admitting to be anything other than a creature of trickery and pleasure, and being forced to admit that he's anything more than that means confronting a lot of things he's buried. In a lot of ways, he's become The Trickster and trying to get to the parts of him that are still inherently Gabriel means dealing with parts of himself he's tried to openly leave behind, so he keeps away from it as much as he can- he kept up his facade all the way up until the point where it became clear the boys weren't falling for his jokes anymore. He became a creature lower than his station, because that creature was what he needed to be- one who is actively involved in the lives of mortals, but one who delights in sheer amusement and little else. He drowns himself in distraction, dancing through life in a haze of mindless self-indulgence and meaningless pleasure. This is how he manages. This is how he deals with the fact that he turned tail and abandoned the people he cared about- by pretending he really doesn’t give a damn.
His sense of morality is skewed, but not completely absent. He believes firmly that every person he screws with deserves it and would never hurt anyone who didn’t deserve it or didn’t have a lesson they needed to learn. The people he kills are people who couldn’t have changed their ways, no matter what he tried- the ones who survive his pranks are the ones that there’s still hope for. He would point out to anyone that the people he doesn’t kill greatly outweigh the ones he does- it’s just that no one pays attention until bodies start turning up. He firmly believes what he does is right and that he's perfectly in his rights to deal out this brand of justice- sorry, he's an angel. It's what they do. He's not a hero and he would never refer to himself as such, even if he does have an almost vigilante thing going on, if you take away the fact that he clearly enjoys giving people what's coming to them that paints him in a heavily negative light. He's not a bad person. He's not a good person. He doesn't pretend to be either. He's just Gabriel.
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All of this, however, is part of his public persona, because it’s important that Gabriel keep his true feelings hidden and thus he does everything to avoid looking like he gives a damn until forced into the open. There's so much to him that it's almost impossible for one person to peel back the facades he puts up and that makes it hard for people to get close to him, due to the fact that he pretends to not care about anyone or anything and uses his sarcasm as a defense mechanism- Dean calls him on this in Hammer of the Gods, even noting it's something that they share (although, they have completely dissimilar reasons for sharing it- Gabriel uses his to maintain his standing as a dominant force). Getting past all of his defenses is something that just doesn't happen (except in rare cases), because anytime someone does, he slams the walls right back up again, although, by that time, he's probably already snapped and shown that he's affected and given himself away, anyway. He is extremely fond of denial and does not like admitting to be anything other than a creature of trickery and pleasure, and being forced to admit that he's anything more than that means confronting a lot of things he's buried. In a lot of ways, he's become The Trickster and trying to get to the parts of him that are still inherently Gabriel means dealing with parts of himself he's tried to openly leave behind, so he keeps away from it as much as he can- he kept up his facade all the way up until the point where it became clear the boys weren't falling for his jokes anymore. He became a creature lower than his station, because that creature was what he needed to be- one who is actively involved in the lives of mortals, but one who delights in sheer amusement and little else. He drowns himself in distraction, dancing through life in a haze of mindless self-indulgence and meaningless pleasure. This is how he manages. This is how he deals with the fact that he turned tail and abandoned the people he cared about- by pretending he really doesn’t give a damn.
His sense of morality is skewed, but not completely absent. He believes firmly that every person he screws with deserves it and would never hurt anyone who didn’t deserve it or didn’t have a lesson they needed to learn. The people he kills are people who couldn’t have changed their ways, no matter what he tried- the ones who survive his pranks are the ones that there’s still hope for. He would point out to anyone that the people he doesn’t kill greatly outweigh the ones he does- it’s just that no one pays attention until bodies start turning up. He firmly believes what he does is right and that he's perfectly in his rights to deal out this brand of justice- sorry, he's an angel. It's what they do. He's not a hero and he would never refer to himself as such, even if he does have an almost vigilante thing going on, if you take away the fact that he clearly enjoys giving people what's coming to them that paints him in a heavily negative light. He's not a bad person. He's not a good person. He doesn't pretend to be either. He's just Gabriel.