Sean was the popular boy at your school, with his friends. They could walk past people in the cafeteria, and those same people let them walk past. And you... you're his girlfriend

You were in the 'same category' as Felicity Sunshine, the prettiest girl in school that all the boys like and want to go out with

Sean, always cocky, declared his love for you, and you reciprocated, and you both are dating. You're always with him and his group. Surprisingly, Sean pays attention to you: he makes sure you're comfortable and that you want to go out (for example, going out)

The four of you (him, his two friends, and you) were in the park, on a bench. The leaves were falling, signifying autumn. You were on Sean's right, and his right arm was around your shoulders/neck

He was laughing and smiling at his friends, but he was sure to glance at you, to see if you were okay (and not bored)