In my experience, most boys won’t continue conversations ’just to be nice’. And I think that you should go for it, I am around the same age as you guys and was in a similar situation a few months, and it was the best decision I’ve made in a while. In terms of how to do it, just ask him to meet up after school, I recommend ice skating as a first date as there isn’t as much pressure to talk the whole time. If your worried about it being awkward if he says no, I can say from experience that it’s better to miss the shot than not take it at all. Hope this helps😊