Oliver spends all day with Tess. There are two places he goes Luthorcorp/Queen Industries and watchtower, which are the two places she goes. So, he sees her all day, everyday. not that he's complaining.
It's only, because of this he notices things. Like the way her hair falls across her shoulders, or the way she runs her hair through it when she's annoyed. She clenches her teeth and squints when she concentrating. And every little thing sends his heart racing and shivers down his spine. The worst part, both of these are extremely noticeable. It's truly amazing that she hasn't noticed them. Maybe she has and just chooses to ignore them, I wouldn't put it past her.
He's tried so hard not to notice or at least not fall totally in love with these little, trivial things. But he simply can't help it. And unfortunately, not only can he not not fall in love with these things, he can't seem to muster up the courage to tell her exactly how he feels. Or how these little things drive him completely insane.
It's hard to see her everyday and know she's not his. Or that anyone could come and sweep her off her feet. Oh no, anyone. That wouldn't be good. That would hurt, like, a lot. That's a scary thought.
But it's harder to say something. Yeah, he doesn't want to do that either. What if she said no? That would also hurt, a lot. Decisions, decisions. Love is complicated. He can't did this, nor can he do that. How do you choose?
Although, he gets satisfaction seeing her turn down guys a million times a day saying she doesn't have time. Wait, that means she wouldn't have time for him. But that's because she's spending time with him. She he wouldn't have time for him because she's spending time with him, yeah, that makes sense. See how much trouble tucking your hair behind your ear can do?
So, he decides, he'll just just keep things the way they are.