How One Lady Facing Homelessness Got Big Money

Graffitied wall in the city with a couch and mattress next to a tree

“I was minding my own business!” 

Ruby, a lady facing homelessness since I met her a few years ago, flared her arms as she told me this. 

She had yet another great story, and I couldn’t wait to hear it.

I bumped into her on one of my strolls, wondering if I’d run into any characters or see some street drama.

My jaw dropped when she told me how she got a big wad of money. With all of the tales she shared about her travels and nomadic life, I didn’t expect his one.

But that’s how life goes… 

You’ll never know when the good fairy will bring you a special treat.


“You got 50 cents, mama?” 

That’s a smart question to ask strangers when you need money. Ruby knows that most people do not have two quarters to rub together, or half-dollars, for that matter. 

Now… When’s the last time you’ve seen a half-dollar?

People carry around plastic—credit cards—and less often cash. Heck, I haven’t had coins or even dollars in my wallet in quite some time. 

“No, I don’t have any money on me today, Ruby. I only have my credit card, but hey… what’s up? I haven’t seen you in a while,” I said.

“Yeah, I’ve been around… You good mama?” Ruby asked.

“Yeah… it was nice to see you again!” I stood there smiling for a moment as Ruby bobbed her head to the beat of music. Then I waved and went on my way.

As soon as I left, Ruby continued cursing at passers-by. 

Every time I see her, she screams at people on the streets. As soon as I call her name, a switch flips, and the funny, friendly Ruby appears.

“What’s your name?”

That’s how I learned her name—I asked

I see her so often and buy her food sometimes, so… why not ask? 

With the most puzzled look, she responded, “Ruby… done nobody ask me for my name… never.”

I told her my name, but she insisted on calling me ‘mama.’

When I walk around the city snapping photos, I learn more about her each time I run into her. 

She ended up here because ‘some government person’ gave her a one-way ticket from Indiana to California.

That’s not the only time she has traveled. She mentions visiting other US cities from time to time.

And about not getting along with others… 

“I won’t stay in no homeless shelter… never,” she said. So Ruby would rather sleep on the sidewalks. 

And I know where she stashes her backpack during the day—she told me once.

Her flannel shirts and jeans come from the local Korean church. In exchange for her worn-out clothes, they give her slightly used duds.

Some days, she doesn’t say much to me because she’s busy hustling money from people on the streets. On other days, she’s an open book, sharing interesting stories about her quests.

“Don’t let that homeless lady in here!”

Fenced off city park in California where people facing homelessness were removed by city workers

The last time I bought Ruby a burger from the sushi-taco-burger joint down the street, they screamed this. 

So I ordered some grub for her while she stood outside watching from a safe distance. The owners pointed fingers at her and told me they had ‘banned’ Ruby for life. 

Nevertheless—she still finds a way to indulge in their juicy cheeseburgers and greasy fries.

Ruby has told me countless stories of people pushing her away and telling her to leave. She must have gotten used to it.

Once, she and another man found a sleeping spot beside the police station. Street lamps lined the street, and police cars made their rounds, making the street appear safe.

But that was short lived…

Within a few months, other people started sleeping on that street, and before Ruby knew it, tents filled the sidewalks. 

So, the city swept that street clean and posted signs that banned her and other people facing homelessness from sleeping there ever again. 

After that, Ruby found refuge in the corner of a little park. When I first saw her there, two other men had pitched a tent nearby but stayed hidden. 

Within a few months, the area grew into an encampment with cardboard homes and makeshift fortresses.

In no time, city workers came by and swept all of this away, and Ruby got banned once again.

“I find a good place and people ruin it.”

Now, she had to find another place to sleep. Sometimes, her friend allowed her to stay in his apartment, but she liked the streets. 

Carrying only a backpack, sleeping bag, and pillow, Ruby searched around and found a place across from some lavish apartments to rest. 

The streets were empty around 10 p.m. 

The street lamp flickered and buzzed above her. Sirens wailed in the far distance as cars passed Ruby’s solo camping area every now and then.

Before bed, she propped herself against the wall, sat in her sleeping bag, and bobbed her head to music from her radio. 

Then Ruby heard the click-clack of dress shoes approaching her on the sidewalk. They grew louder and louder and finally stopped at her sleeping bag. 

A middle-aged man in a suit towered over her as she raised her head.

She turned down her music and locked eyes with the man as he loosened his necktie. Pulling her sleeping bag up, she tightened her fists.

Then the man shoved his hands in his pockets and asked, “Can I sit down and join you?”

Ruby furrowed her eyebrows and grabbed her backpack. The straps and buckels scraped the sidewalk as they dragged.

Then the man hunched his shoulders up to his ears and cocked his head to the side.

“For what? You know I’m homeless… right?” Ruby asked.

“I know… is it okay if we just talked?” the man asked. He sat next to Ruby on the sidewalk. “I just need someone to talk to right now.”

Okay…” Ruby said. 

She looked around to see if a movie crew was filming this. Was there a YouTuber hiding in the bushes? 

Nope… just the two of them sitting together on the black-stained sidewalk late into the night.

“I was scared at first. What did he want?”

City streets in Los Angeles California at night with street lamps lining the street and city bus in the distance

The man talked about his sad journey through life. He hated his job and his tyrant boss. His career had taken a turn for the worse. 

The life that he knew was a sham. 

His friends… were not real friends. Toxic people teased and used him. His girlfriend stressed him. 

And there he sat before Ruby, on the verge of tearing up. 

She nodded her head and listened the whole time. This man in the suit seemed to have everything—money, friends, a relationship, and a home. 

And Ruby thought she had problems… 

The way he moaned about his drama made Ruby think that her problems living on the streets and facing homelessness were not so bad after all. 

Her life seemed so simple compared to his.

Then, after two hours of talking, the man said, “Thank you for listening to me. You’ve been a good friend.”

He reached into his wallet and handed Ruby $300. Then he stood up and disappeared into the night. 

Ruby sat in her sleeping bag, staring at the wad of money. She wondered if this truly happened.

Was it all a dream? 

No… this was cold, hard cash in her hands!


“But… I didn’t do nothing!”

“I couldn’t believe he gave me all this money! I was just listening to him, and that was it,” Ruby said.

“Maybe you did what no one else has done… listened,” I said.

Then I asked a billion questions about this guy…

Who was he? Was he drunk? Where did he come from? 

She didn’t know.

All she knew was that when she asked people for change, most people walked on by. Occasionally, someone handed her $20. 

Nobody ever sat down and talked to me… and nobody never gave me money like that,” Ruby said.

“That’s amazing… and what did you end up doing with the money?” I asked.

“I got me some new headphones!” Ruby laughed as she held up her new shiny new toy. That didn’t shock me—she loves listening to music.

And sometimes, a little listening goes a long way.

Updated: November 1, 2024

error: Content is copyright protected.
Scroll to Top