Today I saw the flashiest homeless guy ever.

I have finally managed to stop being so cheap (mostly). I slowly started removing the clothes that didn’t fit me from my closet. I now wear a size medium, but I still have a few Large and even (gasp) extra large shirts and a couple of pants with a waist size 2 sizes too large. I didn’t do it all at once, but  I finally started buying a shirt here and a shirt there. I even managed to stop being such a hood rat and instead of continuing to poke holes in my belt, I actually bought one that fits! I had opened 4-5 holes in the belt so I guess it was time.

Either way, I had intentions of donating my clothes to Goodwill and getting the usual receipt for it. Thing is that when I do my taxes, I never seem to have enough to itemize this as a deduction. I don’t do it for the deduction, but it sure the hell would be a great perk. I couldn’t quite muster the energy to drop off the clothes, so I kept traveling with it in the back seat of my car.

Every morning when I go to work I see the same homeless man, probably in his late 50’s, pacing the same median holding up a sign that says he’s homeless. It finally hit me that I could just give him the clothes (I don’t like giving homeless people money and I usually don’t carry cash). “Excuse me. Do you have use for second hand clothes, sir?” I asked Henry the Homeless (that’s what we shall call him for identification purposes). “What kind of second hand clothes?” I was stunned into silence. Did he want brand names? Was he wondering if I was giving him lingerie? I didn’t understand the question. I leaned over and grabbed my neatly folded clothes and said “this kind of second hand clothes”. “Oh, heck yeah!” Henry the Homeless said. “I don’t have a bag, though” whined Henry the Homeless. “I’m sure you’ll figure something out, sir” I said as I drove when the light turned green. I didn’t think of that, but I should have given him a bag. I felt certain he would figure it out, though.

The weekend went by and I forgot about the clothes I had given Henry the Homeless. Monday was a holiday so I deviated from my schedule. Finally I went to work on Tuesday and took the same road I always do. I suddenly remembered giving Henry the Homeless the clothes. How could I not? There he was pacing his usual median with his sign while wearing unwrinkled khaki slacks and a striped button up shirt. I felt certain I had done the right thing giving this to him rather than Goodwill. Henry the Homeless looked sharp, too. He was likely the sharpest dressed hobo on the block. That was one of my favorite shirts and it still looked in extremely good conditions.

Henry the Homeless stopped at the end of the median and scrunched up his face before he slowly slid his pointer finger an inhuman depth into his nose. After wiggling about for a while, Henry the Homeless must have captured the prey he was looking for because he rubbed his hands down what used to be my favorite striped shirt all the way down to the slacks.. and he looked relieved. Our eyes met. I looked mortified. The light changed and I drove off. Out of curiosity I found the nearest Goodwill via Yelp. I’m thinking I’ll drop off clothes next time.


Come to think of it, maybe I can do other things for Henry the Homeless and I can keep you posted. Who knows? He can be a mini celebrity.

  1. Deb says:

    Gross funny!

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