I like this boy but...?

he is really desperate, that isn't the problem, but he used to like me but we realized things were never gonna work out. I REALLY like him and have now for about 5 months and i think he thinks we went out for 3 months. We don't really talk anymore but once in a while we will text all day (we go to diff schools) and i really miss him. He plays hockey and he told me he would go ice skating with me sometime in december... December is here and we never brought it up... would it be weird if i texted him saying remember when u said we should go ice skating? wanna go _________.? and also what should i do? should i wait for him to text me.... he usually texts first...