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Yesterday I deplaned after a six-hour flight, picked up my bags, and hopped on the Orange Line home as I usually do when I fly into Midway. At some point just north of the Loop after I’d changed trains, a young man walked on and began to talk loudly in a train full of people getting off work.

At first I did not realize he was addressing other riders. I thought perhaps he was on the phone with an earpiece, or maybe he was just another one of the many rambling individuals who so often hop on the train. But then I realized he was asking for help. He says he was kicked out by his alcoholic father after they had a fight, that he had been sleeping under a Blue Line station, and that all he is asking for is money for a train ticket so he can get to a relative’s house in Rockford. The ticket is $18.60. He has $5-something. He makes his plea but does not go around holding his hand out. All he does is stays by the door through which he first entered and says he will do anything for that train ticket. He holds out his cell phone, calling it the only valuable thing he has, and offers it up to anyone willing to pay for the ticket.

And then I saw something I had never seen in Chicago before. Someone got up to give him money. Others who couldn’t get up without disturbing the person next to them called him over to give him money and offer words of encouragement. And as for me? I sat there, with the March copy of The Atlantic in hand, pretending to be immersed in the final essay of Christopher Hitchens but actually trying to decide whether or not to give him any money.

A curious observation: those who gave money and advice to the young man were mostly those who looked like blue collar workers. Not a single person in a suit, not the guy reading the financial and managerial accounting for MBAs book, not me.

It was a struggle. I often given money to individuals who are always at the same spot everyday, people who I see often. Or sometimes I’ll buy a copy of StreetWise (a newsmagazine sold by homeless or at-risk individuals here in the Windy City). In Europe I had a daily limit of 2 Euros, and mostly only for those who were playing an instrument or otherwise displaying a talent. But recently I’ve tried to heed the advice of avoiding giving money in order to discourage panhandlers, especially aggressive ones. And so yesterday as I sat on the train, I struggled internally as to whether or not he was making a truthful plea or if the money was going elsewhere.

During this whole time he is apologizing for swearing, talking about how embarrassing it is for him to be asking for help, and repeatedly apologizing for interrupting everyone’s peace. And then, without further ado, he left our train car and crossed into the next.

That thought of whether or not I should have helped him out plagued me the rest of the way home. In a world of schemers and scumbags, it’s hard to really trust the word of strangers. Yet, why then, did I feel a pang of guilt for not helping him? Perhaps it is the guilt of circumstance, of being privileged in comparison to him. Perhaps it is because I have a soft spot for those in need of help. Or perhaps it was simply his age, seeing how he could well have been one of my friends under different circumstances.

It still churns in my stomach and makes me wonder, how often we do help, and how often we do simply, carry on?