You stood out in the crowd.
Everyone else looked like someone that fit in with the scene; cigarettes and joints being passed around as often as the beer bottles were, money circling around the crowd before it found its way into the betting pool.
Jason could tell, then, that it must have been your first time here, and he couldn't help but wonder, even in the midst of chaos that came before a race, how you'd manage to stumble upon this side of Gotham City at this hour. It was one of those things that you found on accident or you heard down the grapevine from people that talked when they should have stayed quiet.
He didn't know why he cared at all about what some stranger in the sea of people betting on his downfall or on his win thought about his performance, but something nagged in him about you. Jason wanted to do good enough to keep you coming back. Wanted you to become as familiar a figure in this scene as he had, once under his alias of Robin and now under Red Hood.
Jason's mask was over his face, keeping you from properly seeing him, but it did nothing to hide the clear interest in the way that he regarded you. He pats the hood of his car before he gets in, testing if it was really him that your attention kept getting drawn to, and it was.
Bet on me, he wants to say to you, but he doesn't want you to get involved in this mess of organized crime and sketchy gambling scene.
It's no surprise that he wins the race, and it's no surprise that his eyes find you as the crowd swarms him in the aftermath of his victory. He doesn't show his face to any of them, and won't, but he does tip the mask up a little so you could see a little of the face behind it.
"Wanna go for a spin?" Jason asks you, nodding back toward the car he stood in front of. He keeps the mask lifted, just enough so you can see the beginnings of a smile on his mouth, but not enough to yet show the scar on his cheekbone. "Promise I'll make it worth your while, angel."
Jason was willing, as long as you were, to take this risk on you.