I work at a small private school. All of the teachers are very friendly with each other. I have had the chance during school functions to see and talk with one of the teacher's brothers. He always seems interested in me when we talk ("You look really nice."). I have two questions: Would it be appropriate for me to pursue coffee or something with the brother, to see if we might click? The second question is more difficult: My co-worker, her fiance, and children currently live in the brother's house, so even if I got his number my co-worker might answer the phone. How (if you would) would you go about this situation?