Thank you both for your replies. I have too thought about if I should initiate any contact. I just don't know how to approach it. I don't want to give too much information but she is a teacher at the school my kids go to (not their teacher). As you can imagine there isn't a lot of time for chatting. The encounters i've had with her have been while she was in the lobby and waiting for another child, inside on a break, etc.

I feel like she is into me, but i've never been good at understanding advances (most times I have been set up or asked out - like my wife did when we first dated). If I were to be rejected or misread the situation it would be hard to show my face around their again with other teachers, parents, friends we've made, etc.

I take it if she was interested in me, I would somehow have to initiate the conversation? I would assume it would be hard for her to approach me if she was interested since I am married.

One thing I had thought of is casually emailing her and thanking her for something (like today she helped direct my youngest to where my oldest was) but not mention anything about the interest from me to see how she replies. Our child care has a group email list but am still thinking that would look way to desperate. Thoughts?

This is all so complicated for me and I know I sound like I deserve nothing. Like in my last post it is a mix of wanting to be happier, but with guilt for my family.

Thanks for listening.