Sharing my Faith

On Monday, Krystal and I went to the Walnut-Locust area. I had no idea it was that huge. Around the middle of the area, we met this guy named V (that's what people called him). He was in pretty clean sweats and a hoodie, didn't have any bags w/ him, and he looked pretty clean. I thought he might have even just been sitting down there just chilling. But as we talked to him, he told us about how he was on the streets for two years. He just couldn't find work and he was just looking for hope.
We asked if he believed in Christ and he said no, so we walked him through the Gospel. Afterwards, we asked if he wanted to accept Christ right then, but he said he would think about it and wanted to figure stuff out before he made that decision. I felt it was important for him to know that this grace and hope is a free gift for sinners and not people who have earned their way to a certain spirituality, so I told him that one more time. He said the same thing, and after a prayer together, we went on our way.
Afterwards, I was thinking about how necessary and natural it was to share the Gospel with V. I was able to look him in the eye to tell him straight up what it was about. He needed hope, and Christ is the ultimate hope. But why does it work like that for a stranger I met but not for my friends and co-workers? Why do I shy away from sharing my faith to the people I know and care more about b/c I know them? This has been a challenging thought for me. Just as we pray sometimes when we close on Monday nights, I pray that Diakonos is not just a Monday night thing. Praying for that boldness and that same reasoning for sharing our ultimate hope w/ others.
Will give an update soon about how sharing my faith w/ my co-workers go!