Talking with Jesus is an adventure. He will question our motives and be bluntly realistic and challenging while always respecting our dignity.
For example, a person asked Jesus: "Teacher, what good must I do to possess everlasting life?" (Mt 19:16) Jesus responded by disagreeing with the use of the word "good" (see Mk 10:17; Lk 18:18). We are not sure what the problem was, but Jesus may have been questioning the person's motives. Similarly, if someone came up to you and said: "Hey, good buddy," you may wonder whether he was selling something or had other ulterior motives.
Next, Jesus told the man to keep the commandments, and the man mistakenly responded: "Which ones?" (Mt 19:18) This was a stupid question. We are obviously responsible to keep all the commandments. However, Jesus did not put the man down and make him feel stupid.
Then Jesus probably surprised the man by mentioning first: "You shall not kill" (Mt 19:18). What if someone approached you and nicely but seriously said: "I hope you don't murder anyone today." Jesus suggested to the man that without Him he could do nothing good (see Jn 15:5) and without Him he could do anything bad.
Finally, Jesus challenged him to sell all his possessions (Mt 19:21). The man dropped out of the conversation and walked away sad (Mt 19:22). Will you keep talking with Jesus no matter what?