um, thanks…
rewind:
Me: (approaches bus stop wondering if I’ve missed the bus)
Random Man: (waiting for bus)
Me: “you been waiting long?”
Random Man: “yeah”
Me: (relieved that I didn’t miss the bus)
Man: “I’m new in the neighbourhood”
Me: (staring down the street for any sign of a bus) “oh, that’s nice”
Man: “I used to live at Jane & Weston”
Me: “oh, yeah”
(awkward silence)
Me: “so you live around here”
Man: “yup”
Me: (still staring down the street to avoid eye contact) “it’s a nice neighbourhood except when the bus is late”
Man: “I’ve had a rough life”
Me: “oh”
Man: “but that’s what happens when you’re poor” (looks me up and down)
Me: (dressed up in my work clothes looking very Bay Street) “oh”
Man: “been paying off a debt my whole life that wasn’t mine”
Me: “oh, I think I hear the bus”
Man: “yeah, it’s been rough”
Me: (false alarm on the bus)
Man: “I was wondering if you want to be my friend. You look like a nice enough person”
(awkward silence)
Me: “Oh, I see the bus”
Man: gets on bus and sits at the front
Me: gets on bus and sits at the back
Man: stares at me the entire trip…creepy
oh, the joys of city life! 
haha! I love this story!