The waitress

[Keith]

I like it, but what would you do if she lingered ?

Well, I'm not really him, but I assume that the character would probably have become shy, stuttered his way through a conversation and lost her without her realising how amazing he was beneath that...
perhaps?

Or would you like a happier ending?

She can see him sketching her in his little brown book and sits down to talk to him on her break, he's shy at first, but then opens up when he starts talking about his art, becomes comfortable and asks her to be a traitor and have a coffee someplace else, with him.

Or She's really old has a hairy mole on her chin and wears bright red lipstick because she can, she asks her what she's drawing and they become great friends. I prefer your happy ending, I'm a sucker for happy endings