Smash, without question. She seems like a nice woman.
As far as her wearing the same pants, there's nothing wrong with wearing the same pants, jeans, etc every day as long as they are clean and orderless. If she was wearing the same shirt every day, then it might be a different story, but also, a lot of people tend to own many of the same pair of pants, jeans, etc, so it's hard to tell if they're wearing the same bottoms from the other day.