In the gospels we see (among other things) the developing relationship between Jesus and the disciples. Natural to any relationship is dialogue, with Matthew 18 being one example. Here and elsewhere we see Peter asking a question - in this case a hard question about forgiveness.
In a crowd one can only talk about the overall concepts, perhaps with an illustration or two. In a smaller group, or one to one, you can wrestle with the actual grit of everyday of life, e.g. offence, hurt, forgive, and hurt again. Perhaps you can imagine Peter complaining 'but what about him, I forgave and then he did it again!'.
A gathering inevitably generates an authority structure: the teacher with the knowledge and the pupils to learn. The smaller setting allows levelling, being open and honest - more like the Jewish rabbi/disciple model. Friendship takes this further: exploring together life on life. Our western thinking pushes us to the classroom, but Jesus did it with a group out in the context of the ongoing mission.
Yes there was teaching to the crowd, yes also to the group of disciples, but on occasion in the small where friendship opened both space and vulnerability for interaction. Perhaps we need a re-balancing, increasing our emphasis on the one-to-one. That will be very hard for us because a) we are too busy to give people the one-to-one time, and b) we are tuned to be risk averse rather than vulnerable.
Yet Jesus was clearly vulnerable: think of the cost of forgiving without limit ... a cost Jesus knew would take himself to the cross. I wonder if he answered Peter with tears in his eyes?
Some think that questions invalidate our faith, but in reality probing questions are vital for our growth. The good news is that Jesus was able to go with Peter's questioning, and God can take our questions too. God wants us to draw close with raw honesty, and hence our new key question about our own relationship with God:
Key Qn: [UP] Are you close enough for hard questions?
Challenge: In your triplet wrestle with a question
Can you bring your questions to God? Are you able to wrestle with them, and sometimes just let them sit before Him?
The simple thing for us to remember is that friendship provides good conditions for growth - the ability to exchange and wrestle with thinking in the context of everyday life with its hard realities and complexities. Making space for another to share life with you will create the environment for them to see your way of being, ask about it, and develop for themselves.
Ultimately Jesus drew disciples close and called them not only his friends, but friends of God (see John 15:14 - 15). This was because he enabled them to know his Father's business. Our role as disciples who make disciples is to draw others close to Jesus, helping them discover and learn for themselves the Father's business, that they too will be friends of God.