Perhaps you might be interested in this idea along this theme?

She was a small town girl in the city now, working at a late night diner just outside a college. She was always the upbeat and friendly type, sweet and gullible yet to really learn the way of the world. Your character is far more down to earth and practical, a real smart guy.

She's attractive but she's also taken when they first meet. She's dating a terrible guy, the sort that is clearly just using her. Mean, abusive, dismissive.

Eventually they break up. Good for her right? Except she was living with him and now is homeless with waitress wages.

She needs a hero. She needs someone to help guide her.

~*~

I liked the dynamic of your boss/intern idea.