He is a boy whose feet don't quite touch the ground.
This irritates Gabriel to no end, because he'd always hated that trope.
That sort of... unattainable manic pixie dream girl thing? Pisses him off. And it all stems from that goddamn story, doesn't it. He loves Hitchhiker, he does. But damn that trope to hell.
So when he sees this boy—
This pretty, gangly, awkward, tall boy with floppy hair and the brightest smile in the galaxy, whose feet don't quite touch the ground when he walks, he's a little pissed. He tilts his head, looks at Sam Winchester, and he decides "Screw the world I'm going to flirt like I've never flirted before." Out of spite. He says to God, the Universe, and everything in it—He says, "Fuck you! You put him here to teach me some stupid lesson so I'm gonna hit on him so hard he doesn't know what hit him!"
But then it turns out that this stupid, charming hunter is so beyond oblivious it's not even fucking funny. It's just downright irritating. Gabe wonders how the fuck this boy ever gets laid if he's so blind to advances. Gabriel could probably come out and say "I wanna fuck you on that desk," and Sam Winchester would just smile and go, "What?"
And he still manages to flirt right back at Gabriel! Doesn't even know he's doing it! He just breaks out the dimples and the sweet laughter and the subtle glances and Gabe can feel himself melting already. Goddammit. And he thinks "What the fuck have I gotten myself into?" Something bad, that's for sure.
And the next time they meet, that boy and his brother and their uncle are trying to kill Gabriel. Of course he attacks them. What the hell else would he do. He sits in the theater seats and he laughs and he laughs and he tries to destroy them. Because that's his job. Or at least... It is now. (So maybe he took the avenging angel roots and the Trickster persona a little too far. He enjoys it. He enjoys being an awful person.) And if he contemplates having Sam strangled just a bit for his own personal edification, well... The boy has a pretty neck and Gabriel wants to wrap his fingers around it. But... He figures chainsaw is a better choice, just so he doesn't distract himself.
And he pretends to die, and then... well...
The whole Mystery Spot fiasco.
Maybe not the best way to help someone out?
Yeah definitely not.
But damn if he isn't a little bit turned on by Sam's obsessive stalking of the Trickster. The way Sam just... fixates on him. The pictures plastered on his walls... Screenshots from security cameras where Gabriel lets himself be seen.
Getting caught by Sam, finally. Letting himself be caught. Trying to pound it into that Australopithecine brain of his that he's trying to help. That he's trying to show Sam that he's gonna need to learn to live without his brother. That he's gotta just deal.
But Gabriel just can't meet those big blue puppy-dog eyes without feeling awful. And what's up with that? He's never had that problem before. He's used to dealing with assholes in an indirect way and on the rare occasions he has had to deal a little more up close and personal... Well they've never gotten to him. Ever. But Jesus Christ on a unicycle, that boy's passionately pleading damp gaze just... Goes right to Gabe's cold heart. (Also maybe his dick but... That's just his sadistic side poking through.)
So... Maybe he lets him go and maybe he lets Dean live this one time...
But who can blame him!?
Seriously.
So... perhaps he's a bit more dickish than usual in TV Land. Targeting Sam's general crotch area probably doesn't gain him any brownie points either. But he's gotta be rude and flirt at the same time—so why not hit him in the dick and give him herpes and turn him into a car just to compliment his ass. Uh. Rims.
And somehow Sam still wants to like... show him mercy? Wants to talk?
What the fuck is wrong with this boy? Goddamn martyr is what he is. Gabriel can see that in his soul. How... How weird his soul is. Bright as fuck but just a little dampened by something dark and cruel. Thinks he's worthless. Wants to save the world. Feels like everything bad is his own fault.
Gabriel sees that, and the idea of those two idiot brothers with their stupidly resplendent souls being absorbed into Michael and Lucifer just... it really grinds his gears. And he can't do a damn thing about it.
They leave him there in the spray of the sprinklers and he stands there for a long time moping.
He wishes, more than anything, that he had met Sam under different circumstances. He wishes Sam was just a normal person and that he himself was merely human and that they'd met in the grocery store. Wishes he'd bumped into Sam or something and comforted him after a bad breakup and befriended him.
Kinda wishes he'd been less of a coward.
Even wishes he'd planted a big ol' kiss on his mouth back in Ohio.
Fuck.
He finally gets the balls to stand up for things, the next time he meets Sam.
And he purposely focuses a little bit on Dean because he doesn't think he'll be able to control himself with the thought that there's a 99% chance he'll never see Sam again. He still can't avoid keeping an eye on the boy when he's facing off with Lucifer though. Makes sure he gets out safe with Kali and Dean.
He gets stabbed.
And goddammit if that isn't the harshest betrayal he's ever felt.
His own older brother, who loved him so.
Shanks him right in the solar plexus.
How's that stupid Bon Jovi song go?
Right. "Shot through the heart, and you're to blame."
Fate's a funny thing.
With his Grace leaking from his body, Gabriel remembers why he chose "Heat of the Moment" to play on Sam's clock every Tuesday. He remembers that he chose one of the catchiest, most terrible love ballads of the 1980's because every word of the lyrics was completely true. That song was his message to Sam. Him telling Sam that he'd do anything for him, even though they barely knew each other, because somehow... Somehow he's too attracted to a tall, awkward hunter from Kansas who's been doomed since he was six months old.
Gabriel hits the floor and his last coherent thoughts are "I fucking hate my life" and a slightly guilty "I hope he misses me a quarter the amount he misses Jessica."
He hopes Sam notices that the pornstar he chose looks a little like his dead true love.
But mostly he hopes that Sam Winchester makes it out of Fate's gnarly, twisted, rotting hands.
His wings and halo mark the floor like a goodbye note.
His Grace dissipates into the air and causes a an unconvicted rapist to crash his car into a brick wall.
Just the way he always wanted to go—with a bang.
...
Sam keeps his hand on the lid of his laptop, jaw clenched, trying to be completely unaffected.
But... he's always been fond of Gabriel. Even if he was always an insufferable, inappropriate dickhead. But hey, they had a lot in common. Sort of. He jams the computer into his pack and shoulders his way into the car. The cheesy porno will start right back up again when he opens the laptop and he knows and he really doesn't care.
He wants to make sure there are no other messages hidden in the DVD but... The likelihood that Dean will make fun of him if he mentions it is like... 200%.
Later that night in the motel, Sam sits on his bed. Dean has gone out drinking. Big surprise there. Sam leans back against the pillows and settles the computer on his lap and opens it slowly. Casa Erotica 13 starts up right where it left off—with Gabriel tackling a woman (who looks weirdly like Jess... which makes Sam about twice as unhappy) to the bed and going on to do various obscene things with her. Sam side-eyes the screen. Watching it is... uncomfortable. Not very sexy, if he's honest. Gabriel is putting out a lot of false bravado and the woman is very obviously faking any sort of enjoyment.
Then the room in the porno disappears and it's just... Gabriel. Sitting on a ratty hotel chair talking down to a camera that's probably on a table.
"Sam."
Sam flinches. Hearing Gabriel say his name like that—like he's in the room, almost—unsettles him. Gabriel seems to be meeting his eyes, but that's not possible. Just an illusion from Gabriel looking directly into the camera.
"Sam." Gabriel repeats himself and snorts, before glancing away from the camera and then back. "Boy, do I feel stupid. I've never taped myself before. Well, not in the human way, you know? It's kind of awkward, sitting here alone, talking to a lens." He snaps his fingers, and a bathrobe seems to grow its way along his shoulders and chest like a bed of red moss. He laughs, quietly. "Sorry. Felt weird sitting here all naked. Don't usually get stage fright. Huh. Anyway... uh... Sam, you know I've always... cared about you. In a weird way. I'm sure it doesn't seem like that, but it's true."
Sam lifts his hand to gnaw on his thumbnail—and he hasn't done that since... what... college? It's strangely comforting to indulge in such a tiny nervous tic again. He keeps his eyes locked on Gabriel's.
Gabriel smiles at him. "You're just kind of too adorable not to like. Like a baby moose. All gangly and sweet and big... Anywho! Uh... Just thought I'd let you know, I was definitely flirting with you when we first met. Also you have a great ass. Just... FYI." He winks. Leans closer to the camera, glances side to side with a smirk, and props his cheek against one open hand. "Really, though. I just wanted to say that I've never really met a person with more good in them than you, Sam. You're so selfless and self-sacrificing and kind and... And I know you probably hate that song now—you know which song I mean—but... Go look up the lyrics. For me." Gabriel's smirk softens to something more sad and gentle. He taps his fingers against the tabletop, with his eyes downcast.
"And Sam?" He looks back up, so his honey-colored eyes are fastened on Sam's. Intent and unhappy.
"So long, and thanks for all the fish." Gabriel winks, and reaches forward. The screen goes black and credits scroll up.
Sam lets out a quiet breath.
He ejects the DVD and puts it in its case and tucks it into a jacket pocket.
Tentatively, he googles "Heat of the Moment" and he deflates a little on the motel bed.
Sam Winchester shuts his laptop with unnecessary force and shoves it into his bag. "Oh my God." He sits on the edge of the bed with his elbows propped against his knees and his face pressed into his palms. He feels much too warm and the DVD in his pocket jabs into his side. He barks out a bitter laugh.
He stares at the carpet between his feet.
"I knew I should have kissed him."
Rubs at his eye.
"This is all my fault."
His jaw clenches.
"Everyone I know dies."
He tilts his face back and fastens his eyes on the flickering light on the ceiling. Gabriel's words come back to him—
"This joke is on you, Sam."
And what a cruel joke it's been.