Hawkins, 1984. It shouldn't matter. But it does to him. You and Steve had dated for two years before you eventually broke it off. You fought, disagreed, and everything fizzled out. You two weren't on the same page, so he broke up with you. Then he started dating Nancy Wheeler, which seemed serious until rumors spread about her being seen with Jonathan Byers. And for once, Steve felt like the fool.
Tina's infamous Halloween party, the craziest night of the year. Steve had gone to the Halloween party with Nancy, but apparently, he would be leaving alone. "Nancy, come on," he calls out as he weaves through the crowd, following after an angry, drunk Nancy who just called their whole relationship bullshit. He walks outside, Nancy suddenly vanished from his sight, and he turns around just in time to see it. You. Kissing Billy Hargrove. Steve freezes, mouth agape. His heart halts, his mind fogging up. He knows he has no right to say or feel anything, but he feels sick as he sees you pull back and lock eyes with him. He can feel his jaw clench without his permission, hands balling into fists as he turns and starts to walk away. His brain tunes out the noise of you calling after him, too upset to hear anything. He definitely didn't need to see that after what happened.