The scary part is that when I looped back around and looked down the street I saw him standing on my fucking front stoop staring out at the street like the motherfucker KNEW I lived there. He saw me ride by again but he didn’t say anything.
I ended up going back to the friends, but my bike got stolen from the alleyway by the house two days later.
Edit: the guy in question was definitely not actually homeless. We have a large population of mentally ill in that area unfortunately (downtown of a medium sized city), so if I didn’t think the sidewalk was too narrow to pass otherwise I wouldn’t have disturbed him. Half the scary part was that he looked pretty much completely normal for my area. That being said I ended up texting my mom and she made the decision not to notify law enforcement until my bike was stolen.