Cassandra writes, “I am a 24 year old music teacher. I have developed a good friendship with a 19 year old who I met teaching chamber music outside of school. We have begun to see each other quite a bit out of a teacher-student context and get on extremely well. Nothing remotely romantic has happened but when we’re spending time together it really feels like it could. I have no idea how to approach the situation and wonder if I should just wait and see what happens but worry that we might both be too scared to mention it because of the way in which we met and the potential for awkward circumstances?” (Related: I am in love with my much older professor)
While you maybe his teacher (it is clear that it is a casual relationship unlike that of a teacher and student in an academic setting, where these relationships are generally discouraged and institutions have some guidelines on these), in the end, you are also a young woman very close to him in age. Obviously, it is always uncomfortable to approach someone for romance when you do not meet with the specific purpose of dating. The good news is that getting to know someone without the intention of dating is a great way to know the real person (we all become very self conscious while dating and often present a side of our personality that is not always 100% real) and now that you two realize that you have so much more in common, it maybe time to approach each other with the purpose of dating. (Related: Crush on schoolteacher)
I am guessing that this man is also inclined romantically. If you have a high level of trust, being older and his teacher, it is better if you admit how you feel. Considering that he is younger and may hold you in high regard as a teacher, he may be holding off his emotions and if you do not take the first step, he might never act.