Dear Tristan:

Because you are interested in dating him, you can suggest it to him. The risk is that if he is not interested and rejects your suggestion, you may feel hurt and that hurt will damage the friendship, and/or he will feel awkward and that will damage the friendship. After such rejection, even if you tell him: it’s okay, we are still friends, etc., he may be uncomfortable in the future, wondering if you are still interested in him, if you are expecting him to change his mind.

And if he takes on your suggestion to date and then the relationship ends, there may not be a friendship to resume.

I think there is a risk to suggesting dating to him. Maybe he already sensed that you are interested in dating him, based on some hints you gave him.. ?

anita