Jesus did not act as many people might expect, he certainly did not act as the people of his own time expected. Jesus challenged everyone around him. He challenged the sinner to stop sinning and he challenged the religious to stop being religious. That challenge to stop being religious stands even today. Being religious for me is comfortable. There are rules, I know the rules, and I can for the most part comfortably slide through life picking the rules I like. That is because religious rules are manmade rules. Rules like what one can wear at Church or how to worship in Church. Rules like these really have nothing to do with God.
Go and learn what this means, ‘I desire mercy, and not sacrifice.’ For I came not to call the righteous, but sinners.” Matthew 9:13 ESV
Jesus speaking to the religious leaders tells them his purpose, resolve, and intent is mercy. There is no place for mercy in a religious mindset because the rules are more important than people. When the non-religious mix with the religious that lack of mercy makes everyone uncomfortable. Jesus was comfortable spending time with sinners and many sinners appear to have wanted to spend time with Jesus.
And as Jesus reclined at table in the house, behold, many tax collectors and sinners came and were reclining with Jesus and his disciples. And when the Pharisees saw this, they said to his disciples, “Why does your teacher eat with tax collectors and sinners?” Matthew 9:10-11 ESV
So how did Jesus avoid the awkward? How did he cross the divide of someone who appeared as perfectly religious and hang out with people who appeared without religion? How did cultures and people who would not normally share a meal together sit and eat? Jesus cuts through the uncomfortable cultural divide because he loves people even where they are at the moment. He loves his children. He created people (John 1:3) and the good Shepherd has moved heaven and earth to restore the relationship. Eating with sinners is a result of that love in action. It is real, genuine, and trustworthy compassion and the sinners that Jesus ate with recognized it. That kind of love could never be awkward.
Jesus became a servant who interacted with people as they are. He has provided and pointed to the way one should go. What do you think they talked about at this dinner? Did he talk about sports? Did they bad mouth the religious leaders? I imagine that he talked about what was important to those tax collectors and sinners. I imagine that the conversations were similar to others recorded in the gospels where Jesus with compassion would tell them about their future and the better way that only God can provide.
Jesus stood up and said to her, “Woman, where are they? Has no one condemned you?” She said, “No one, Lord.” And Jesus said, “Neither do I condemn you; go, and from now on sin no more.” John 8:10-11 ESV
He loved them first. He befriended them. He showed compassion by being willing to spend time with them in their home. He allows sinners to come as they are without judgment. Religion only judges and has no room for love.
God shows his love for us in that while we were still sinners, Christ died for us. Romans 5:8 ESV