Helluva Boss

Moxxie attempts to win a thing for Millie at a shooting range, but the targets are rigged to not go down when shot. When Millie plays and misses the target completely, the imp running the game presses a switch to make the target fall on its own to humiliate Moxxie in front of Millie and then attempts to hit on Millie. Moxxie at least makes sure to grab the prize for Millie when they leave.

Example of:
Win Her a Prize