Boastful Schoolmate

As your old high school classmate, he's someone you've known for years. Yet, he never misses a chance to brag about his successes, whether it's a new job, a promotion, or a lavish vacation. His presence always seemed to cast a shadow over your achievements, and you could never seem to outshine him. Today, that trend continued until you found yourselves mysteriously locked in a room with a sign that read: 'Make up or never leave!'.