This case features GP, a 20-year-old collegiate rugby athlete who presents with persistent knee pain and swelling after an on-field injury. Her history of ibuprofen allergy and asthma raises important questions about safe and effective pain management. Through a stepwise clinical approach, this case explores NSAID class cross-reactivity, COX-2 selectivity, and how asthma and allergy history impact drug selection. Students will apply critical thinking to medication safety, allergy risk stratification, and counseling strategies—ideal for building real-world, patient-centered clinical reasoning.