if she's a native theres a chance they went to school together but prob didn't hang out because he only stuck to his people but maybe when she moved back to town she went out at the bar he works at and he remembered her name, laid on the charm paired with a free drink which led to their lil fling. which means it would've taken place months ago but we can say they stopped talking since dev was kinda seeing someone and now that he's single again he's sending her that classic, "hey, what's up? i miss you" text