Hobo’s are Stable in their Instability

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I miss the streets on occasion, well maybe not the living arrangements, but  I do miss the people. If you have never had a stable living situation in your life or, if you have never had a stable bonded relationship, you may have no idea they can actually exist.

So a lot of street people lives are incredibility chaotic and messy; drugs and prostitution so prevalent as to be the norm, especially for those under 30. But hobo’s are human and capable of incredible acts of courage and kindness.

The following is a story of a good friend of mine, who has a ton of kindness and guts. I hope at some point she can find the stability I am finally finding within myself.

homeless woman

I always enjoy running into Jessie. Another beautiful heroine addict; blonde hair, sky blue eyes and a body built for sin. In her thirties she is still narcissistic enough to glance at every passing window.

I don’t know much about her growing up, but I imagine her looks are all she felt she had. Anyway with a lot of junkies it is hard for them to see past doing what ever it takes to get the next high, not sure some of them are aware another person in the world exists.

Jessie has been at it a while, and is good at seeing what is going on with other people emotionally. She treat all hobo’s equally and with kindness. Always there with a hug when she is broke, food and beverages when she can afford it.

She makes me laugh, when you tell her she is beautiful, she will say, “It is such a burden,” and get a look on her face like she actually believes it.

She dates a guy name Willard, who I see all the time. He gets his drug money by walking up to literally every person on the street and asking them for money. I have only interacted with him a few times when he wasn’t high. He is friendly as hell, tall, lanky with long curly hair and large lips.

Jesse and Willard are broken up every other week, so half the time I see her she is in immense heartbreak. The other half her and Willard are hanging all over each other, making a lot of folks turn their heads so as not to witness hobo displays of affection.


Jesse may like me a little, I am not sure, she keeps her cards close to the chest. Last time I saw her, she said she had the best sex of her life the night before and it wasn’t with Willard.

In the past that remark would have made me intensely jealous and wanting her all the more. But at 48 I am comfortable with who I am. I don’t get flustered a bit, which is what I think she was trying to do, find and exploit one of my weaknesses if she could.

She doesn’t trick for money anymore, said she didn’t like who she was when she was doing it. Panhandling and stealing are her way these days. When she was on both meth and heroine and expenses were high, she would go out into rural areas and screw migrant workers for 50 bucks a pop. “Shower, fuck, shower, fuck, shower, fuck, 50 dollars, 50 dollars, 50 dollars,” was how she put it.

She has a mother bear aspect to her as well, I have seen her stand up to police and the business class plenty of times if she thinks they are unjustly treating a fellow hobo.


Many times she has sprinted by me on the streets with a look of great fear on her face. Sometimes she will throw her stuff in my shopping cart as she sprints along and then pick it up later that night. Sometimes I will carry her stuff on my cart for months, wondering what the hell happened to her.  Then there she is, seemingly unfazed by the jail or rehab time, and happy to chat for a while.

Peace to you wherever you are Jessica, and God Bless you.

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