The Homeless Guy said “Not Everybody Can Carry That Look Off”


Wednesday night I was at my liquor store downtown waiting in line to buy some craft beer as a reward for the run I was about to do. The guy ahead of me in line had a bottle of vodka in one hand and a ten dollar bill in the other. He was a homeless guy that I have seen in and around downtown for years. He turned to me and said, “You know you look just like those guys in the old time photographs. That cap and a sportcoat and khaki slacks. You know not everybody can carry that look off but you can.” So I said thank you very much. He asked, “So what kind of cap is that?” and I said that it was called flat cap and a friend from Uruguay got it for me and I love it because it was pretty darn warm.”

So he said “Really” and asked to look at it and so I handed it to him and he said, “No wonder it is warm, it is wool felt.” And I said, “sure is” and he handed it back to me and turned his attention to the clerk as it was his turn.

In a genial manner he told the clerk “Hey, that woman working here this morning said that I can only buy something once a day from you guys.” The clerk said, “That’s right sir we aren’t allowed to sell to the same person twice in a day.” So my new friend said, “Well you know that makes it kind of hard on me because I go through two of these a day” as he held up the bottle, “and I don’t want to be carrying one around all day. You know what I mean?” The clerk said, “I am sorry about that sir.”

And then the clerk said, “You want this in your backpack sir?” and the my guy said “Sure lets put it in there” and while they are doing that he says, “I haven’t decided what I’m going to do yet. My daughter,  I haven’t seen her in 17 years is flying in and said she is going to find me and I don’t know whether I should meet her or just go get drunk. What do you think?” The clerk said “I think you should go meet your daughter.” And I said, “I vote for that plan.”

The guy laughed and said, “Well we’ll see what happens, you guys take care.” And off he went out of the store.

For some strange reason, the guy made me feel good and bad at the same time. I have not met very many people so open, direct, and non-defensive as this guy.

Have you ever had a homeless guy make you feel good about yourself?

10 thoughts on “The Homeless Guy said “Not Everybody Can Carry That Look Off”

  1. JennJilks

    I used to encounter people like this in Toronto, where I grew up. I took one to the restaurant and bought him a coffee. Another time, a guy was panhandling in Nepean, and I took him to the fast food spot nearby, bought him lunch!.

  2. genie

    I, too, find this story you told so well happy yet very sad. But it is the story of so many lives this day in time.Here we have a gentleman who obviously is educated but is still homeless. I would be scared if my daughter was coming to see me and probably would not know any better how to handle it than he is…questioning it all. I think you and the clerk gave the answer I would have given and I love that picture of you in the WOOL FELT hat. This is a very touching post. Thank you for taking the time to share it so beautifully with all if us today.

  3. Gaelyn

    What an amazing experience. I talk to people in stores all the time, but never had a conversation like this. Seems you were all at the right place at the right time. BTW, he’s right about you carrying off “the look”.

  4. DeniseinVA

    My heart goes out to both this man and his daughter. I hope they found each other. Alcoholism is a tough road for those afflicted and for their families. You do look good in your flat cap.

  5. Sallie (FullTime-Life)

    It’s all about acknowledging other people as fellow human beings. When you’re not afraid to step out of the comfort zone of being surrounded by people just like yourself, then any ordinary day can be an adventure or at least a learning experience. Maybe your encounter was just that for the homeless guy as well! (And he is right about you and the hat, by the way. )

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