I can assure you the game is not bugged, as I've just tested it. Popcorn's route is designed in a way as to where you're really only allowed to make one mistake, so that's likely why you've been having so little luck.
Popcorn can be a hard character to read. You being a "tryhard" wasn't the full, ingame reason as to why Popcorn didn't want to date you, it was just a hint on what you might've done wrong. There are obviously some menu choices you'd have to make where maybe the "aggressive" option wouldn't be the best thing to do. The best hint and advice I'm willing to give is, whichever provokes the most positive response from him, whether he's smiling or talking more is usually the way to go.