Headaches over chai lattes and paperwork.
i put a lot of work into something stupid

The sharp wind outside the bar is nice.  Leaning against his car on a Friday night seems like a new brand of pathetic because you don't go after a girl who is dating her ex-fiancee and in love with someone else and you all work together.  Even though he never went after her, (ask anyone) and she has no idea it rings of high school when he knew that tomorrow everything would have blown over (but that's not how it works here). 

He had been pretty sure he was over her because he'd been able to look at someone else (and bring her to a wedding for crying out loud) but one word form her and he's spinning again. 

He breathes out and watches the condensed moisture float upwards and dissolve in the sky.  He shouldn't feel this way but a yellow duck in the back seat says this is how it should have been. 

Everyone else is inside, and he's outside and he feels like this should be symbolic, like him sitting at the annex back alone should mean something or reflect on his character. 

He's about to give up and leave when he hears a crash and the ring of breaking glass and sees  the sliver of yellow when Pam rushes out the door.  He doesn't know what to do because the rules on this kind of thing aren't exactly in existence and he doesn't want to show her "Toby is awkward Vol 2".   But she looks upset so he can handle it. 

He almost-follows her to her car and puts a hand on hers when she tries to get in.  She looks up and things don't seem so pointless or stupid. 

'You don't have to say anything' is better than 'it's okay' because he knows it he/she isn't.  And leaning against her car, silent isn't the worst thing that could have happened.  He knows holding her after she was with someone else doesn't count but it's still something.