Jesus spent so much time reaching out to so many others during his ministry, choosing only two passages is difficult.
When Jesus began his ministry, he chose disciples to be his closest friends and helpers. His choices were not made based on religious training, public speaking experience, or any other criteria that might have seemed likely for the tasks that were in store. Instead, he called fishermen, a doctor, and a tax collector - probably the most unlikely selection of all, given the hatred the Jews felt for those who collaborated with the Roman occupiers. Not only did he call Levi, as recorded in Luke 5:27-28, but
Levi made him a great feast in his house; and there was a large company of tax collectors and others sitting at table with them. (Luke 5:29)
Jesus reached out to groups of people from all walks of life, with a variety of viewpoints about his work. He made a point of making contact with those who were excluded by the society of that time and place. John 4:7-30 tell of his conversation with a Samaritan woman - a shocking exchange both because Samaritans were despised by the Jews and because, in the very patriarchal culture of that time, women were not to be out in public or spoken to except by close members of the family.
The Samaritan woman said to him, "How is it that you, a Jew, ask a drink of me, a woman of Samaria?" for Jews have no dealings with Samaritans...Just then his disciples came. They marveled that he was talking with a woman, but none said, "What do you wish?" or, "Why are you talking with her?" (John 4: 9, 27)