John the Baptist sent two of his disciples to Jesus. It was his anxiety not theirs that prompted the questions. Jesus' answer is experiential, but experience that connects to Scripture. I think that is THE way to confirm faith, experience connected to the Scriptures, not experience alone or the Scriptures in a vacuum. It is true. . . and it is true for me.
John was so rigorous with his religion they thought he had a demon. Jesus was dismissed because he was open to outsiders. Wisdom is proved by her actions. Wisdom necessarily results in actions that will vindicate misunderstood choices.
These "woes" indicate that Jesus knew what would have happened, not only what does happen or what will happen. This is a whole new dimension of omniscience.
Jesus invites us to follow him because he is gentle and humble. He says this right after he pronounces "Woe" on entire cities! Hmmm.