Jesus' Surprising Friends - Who He Spent Time With
Jesus’ Surprising Friends – Who He Spent Time With
When you think of Jesus, who do you picture Him with? Maybe His disciples, large crowds, or religious leaders? But if you look closely at the Gospels, you’ll find something surprising—Jesus often spent time with people no one else wanted to be around.
While religious leaders kept their distance from "sinners," Jesus went out of His way to eat with them, talk with them, and even call them friends. His closest companions weren’t always the most respectable—but that’s exactly what made His love so radical.
Let’s take a look at some of Jesus’ most unexpected friendships—and what they teach us about God’s heart for people.
1. The Tax Collector Everyone Hated (Matthew the Traitor)
Tax collectors in Jesus’ day were seen as traitors. They worked for the Roman Empire, often overcharging people and keeping the extra money. Most Jews despised them.
Yet one day, Jesus walked up to a tax collector named Matthew and said, “Follow me” (Matthew 9:9).
Imagine the shock! A holy rabbi calling a corrupt tax collector to be His disciple? But Jesus didn’t just call Matthew—He went to his house for dinner, sitting with other tax collectors and “sinners” (Matthew 9:10).
The religious leaders were furious. “Why does your teacher eat with tax collectors and sinners?” they asked.
Jesus’ answer? “It is not the healthy who need a doctor, but the sick… I have not come to call the righteous, but sinners” (Matthew 9:12-13).
Jesus didn’t wait for people to clean up their lives before loving them. He met them where they were—and His love changed them.
2. The Woman with a Bad Reputation (The “Sinful” Woman at Simon’s House)
In Luke 7, Jesus was invited to dinner at a religious leader’s house. But the evening took an unexpected turn when a woman known for her “sinful life” came in.
She wept at Jesus’ feet, wiped them with her hair, and poured expensive perfume on them. The host, Simon, was disgusted. “If this man were a prophet, he would know what kind of woman is touching him!”
But Jesus knew exactly who she was—and He defended her.
“Do you see this woman?” He asked Simon. “Her many sins have been forgiven—as her great love has shown. But whoever has been forgiven little loves little.”
Then He turned to her and said, “Your sins are forgiven… Your faith has saved you. Go in peace.”
Jesus didn’t care about her past. He saw her heart—and He honored her when others shamed her.
3. The Thief on the Cross (A Last-Minute Friend)
Even in His final moments, Jesus befriended an unlikely person—a criminal.
Two thieves were crucified with Jesus. One mocked Him, but the other said, “We are punished justly, but this man has done nothing wrong.” Then he turned to Jesus and said, “Remember me when you come into your kingdom.”
Jesus’ reply? “Truly I tell you, today you will be with me in paradise” (Luke 23:39-43).
No time for good deeds. No religious rituals. Just a desperate plea—and Jesus’ immediate mercy.
If Jesus could save a dying thief, no one is too far gone for His grace.
4. The Samaritan Woman (The Outcast at the Well)
Jews and Samaritans hated each other. So when Jesus spoke to a Samaritan woman at a well (John 4), His disciples were shocked. But what made it even more scandalous?
This woman had been married five times and was living with a man who wasn’t her husband. Most rabbis would have avoided her, but Jesus didn’t just talk to her—He offered her living water and revealed Himself as the Messiah.
Because of her testimony, many Samaritans believed in Jesus. An outcast became one of the first evangelists!
5. Zacchaeus (The Short, Greedy Tax Collector Who Climbed a Tree)
Zacchaeus was a chief tax collector—meaning he was rich, corrupt, and hated. When Jesus came to town, Zacchaeus was so eager to see Him that he climbed a tree (since he was short and couldn’t see over the crowd).
Jesus looked up and said, “Zacchaeus, come down immediately. I must stay at your house today” (Luke 19:5).
The crowd grumbled. “He has gone to be the guest of a sinner!”
But Jesus’ kindness changed Zacchaeus. He repented, giving half his wealth to the poor and repaying those he cheated four times over!
Jesus didn’t see a greedy thief—He saw a man who needed love.
Why Did Jesus Choose These Friends?
Jesus could have surrounded Himself with the most respected, moral, and powerful people. Instead, He chose:
A traitor (Matthew)
A socially shamed woman
A dying criminal
A Samaritan with a messy past
A cheating tax collector
Why? Because Jesus didn’t come for the ‘righteous’—He came for the broken.
The religious leaders thought they were better than others, but Jesus said, “It is not the healthy who need a doctor, but the sick” (Mark 2:17).
What Does This Mean for Us?
No one is too “bad” for Jesus. If He could love thieves, cheaters, and outcasts, He can love anyone.
Real love reaches out. Jesus didn’t wait for people to come to Him—He went to them.
God’s grace is for everyone. Not just the “good” people—but the ones society rejects.
Final Thought: Who Are We Choosing to Love?
Jesus’ friendships scandalized the religious people of His day—because He loved the ones they ignored.
Today, who are the “unlovable” people in our world?
The coworker no one likes?
The neighbor with a messy life?
The family member who’s made mistakes?
If Jesus were here today, He wouldn’t avoid them—He’d befriend them.
Maybe it’s time we did the same.