Alan, I don't really think it's creepy. I think it's a sweet gesture and that he himself hasnt been able to convey his feelings. I refuse to think anything negative about him unless OP actually says he's creepy etc. Even then we cant really come to conclusions because we dont know him personally. Everyone expresses their feelings differently.

Not neccessarily the case. I've done a lot of portraits during class because I was bored and wanted to improve my skills, and drawing the people next to me was more out of convenience than attraction. I've even tried drawing people I absolutely loathed simply because their faces were interesting. Unless the boy was using loose paper that fluttered to the ground, I find it hard to believe that OP could actually see the contents of the entire notepad (which would indeed indicate obsession), probably more like one or two pages. He could've just been practising.

The drawings are a little creepy, yeah, but that doesn't mean he isn't a sweet guy. Besides the drawings, it probably wasn't the guy's reputation as being weird or mean or just off that freaked her out so much as the fact that she doesn't even know him.

I'd say it even sounds inkredibly sketchy. Thank you for drawing that to my attention.