What happened after I lent a homeless guy twenty bucks

This is not Floyd, but he is a Floyd.
This is not Floyd, but he is a Floyd.

Before I start this story, I just want to preface it with the fact that it doesn’t have a super exciting ending. It’s not one of those internet stories where I give a homeless dude a hundred dollar bill while recording with a hidden camera, and in turn, he immediately rips it in half and generously shares it with some other dude who’s aggressively more homeless than him and then the internet buys them a house and they become roommates for life.


It actually has a really unexciting ending. So to save you time, I drew a graph of how the story progresses in terms of excitement.


Alright, so earlier this year I moved to SF and got a new job in sales. One night I was walking home from some bar and decided it would be a good idea to practice this pitch I was memorizing for work. New to SF, I noticed crazy people talking to themselves on the street all the time so I figured it would be okay.

I was right.

Nobody batted an eye.

About ten minutes in, this guy comes up to me and says “I know you’re not talking to yourself right now.” I tell him how I was practicing this sales pitch for work and he says “Ok, why don’t you pitch me?”

“Alright. I could use the practice.” So I start pitching this guy while we walked back towards my house together. At this point, I was slightly drunk but was also getting kind of nervous because I barely memorized this pitch and my delivery was pretty shitty. At some points I was jumbling my sentences together and referencing non-existing slides, but he listened and nodded along anyways.

After I was done he gives me some feedback. He told me I talked too fast and some other stuff I can’t remember but it was helpful. I thanked him and introduced myself. It wasn’t until now that I started suspecting he might have been homeless. The dude was actually missing his four front teeth but he was pretty good at hiding it. He tells me his name is Floyd and that he actually was homeless. We start talking about how he became homeless. He seemed like a pretty normal dude. He talked a lot and was very outgoing. He was relatively good looking and had a very likable demeanor. He was probably around 50 so he kept making references to things I didn’t know about, but I just nodded along like I did.

He went to college and played football there. He used to have a pretty normal life, used to work in mortgages, was married and has three kids that are now grown. He told me his twin brother was pretty successful. He said he became homeless because he’s bipolar and got really depressed. I didn’t want to pry so just left it at that.

My conversation with him went a bit longer than I would’ve preferred but I liked him. He showed an interest in me, which could’ve been genuine or fake, but regardless, I liked his hustle. Eventually he tells me he needs $10 to stay indoors for the night. This was in February and it was pretty cold outside. Coincidentally I had a $10 bill in my pocket so I gave it to him. I also gave him my e-mail address and told him to send me his resume and that I would let him know if I saw any job postings that had to do with mortgages.

The next day, he e-mails me and asks me how my pitch went. That was pretty nice of him. I reply telling him thanks for asking.

About a week later, he e-mails me and asks me for my phone number. I give it to him.

About three days later he calls me and asks me what time I’ll be off work. I tell him around 6-7 and he tells me that he will call me around then. Around 6 or 7 he calls me and asks me if I have any socks or sweaters.

I thought this whole process was interesting. He calls me to set up an appointment to call me again to ask for a favor. I kind of liked it.

So I meet him up, give him some socks, old sweaters and this pair of skinny jeans that Beatrice made me buy that I never wore. Inside, I felt kind of bad because I gave him a pack of dress socks that I got for Christmas. The dress socks probably wouldn’t have done much for warmth but I didn’t want to give up my regular socks because it would’ve decreased the number of days between having to do laundry.

I met him up like 2-3 times over the next week or two. I usually brought him some food and some clothes. Every time I saw him, he’d be wearing the clothes I gave him (including the skinny jeans). I couldn’t help but wonder if this guy was doing it on purpose. Like, maybe he didn’t need the clothes and was wearing it as a front because he wanted something from me. Still wasn’t sure, but I was super curious.

So eventually one day he calls me and asks me if he can borrow $30. He says that he spent all the money he has for the month and really wants to sleep indoors for the next few days. He tells me he gets money from the government for his depression every month and he will pay me back in a week when the money comes in.

At this point I am super fucking curious. To be honest I was really torn about what to do. Based on my interaction with him so far, he seemed like a pretty genuine dude. For $30, I could be making his life significantly more comfortable for a few days, but at the same time I could be just getting conned. I thought about it for a while and ultimately decided I would lend him $20. This is because I only had $20 on me. The reason I decided to lend him the money was because he told me he would let me hold his government ATM card as collateral.  So basically, I would lend him the money and get his card in return, then later we would meet up and I would give his card back and he would pull out cash and return the money to me.

So, I meet him up on a Wednesday and he tells me he will call me back on Sunday and return the money.

Sunday night comes around. It’s like 9PM and he calls me to meet up in an hour. Around this time, you kind of start to wonder if it’s safe to meet some stranger out at night to exchange money, but I figured I was in good enough shape and nourished enough to beat up a homeless guy. Also, I was so goddamn curious to see if he would return the money.

Around this time my roommate and her boyfriend were around and I tell them the entire story. We spend the next hour discussing all possible outcomes. My roommate’s boyfriend was super against meeting him up. He basically thought that Floyd was in for some long con and was going to use the money for drugs. My roommate disagreed. We ended up having a really long discussion about all possible outcomes and then homeless people in general. It was me and my roommate against her boyfriend and eventually they made a bet on whether or not Floyd would pay me back.

So at 10PM, I go outside and walk down to the corner. Floyd shows up like five minutes late, says what’s up and we walk to the ATM. He proceeds to pull out like $80 and gives me back $20. I thank him and we part ways. As he’s walking away he yells “HAH didn’t think I’d pay you back huh!?”

I was so happy he paid me back. Arguing with someone about it for an hour before also made the victory so much sweeter. I ran home and figuratively rubbed it in my roommate’s boyfriend’s face. I had seriously thought about letting Floyd keep the money if he was willing to pay me back, but I wanted to develop a long term relationship with him and I figured it couldn’t be done if I just give him stuff for free.

Off note: (Being Iamhellacheap, I couldn’t resist e-mailing Floyd to tell him about avoiding ATM fees. I noticed the ATM charged him a $3 fee and he probably got another $3 fee from his bank later. It’s pretty bullshit how they charge so many fees to people in need, especially since they don’t really have the mobility or resources to learn about how to avoid it. I looked on the website of his card issuer and there were very limited options to pull money out without any fees)

Anyways, eventually Floyd hits me up again and asks me if he could borrow more money. To be honest, he called me a few times but I ignored him out of laziness. The one time he manages to get a hold of me he says he’s like 2 weeks away from getting paid. I meet him up again and lend him another $20. He hands me his ATM card but this time, I wanted to push the limits of our relationship. I tell him to hold onto his card and just call me when he gets the money.

My goal was to slowly increase the trust between the two of us, but I think I might have moved too fast. Two weeks went by and I didn’t hear from him. Eventually more time goes by and I still don’t hear from him. I don’t really blame him for not paying me back since that money will go much further for him, but I was kind of bummed that we missed out on the chance to be friends. I was planning on interviewing him about his spending habits and how he lives off of $500 a month. I thought that would’ve made an interesting article for Iamhellacheap. We e-mailed a few times back and forth but we never really talked about anything significant. He also stopped calling me to borrow money.

Fast forward a few months later, I was walking home at night and saw some dude wearing a sweater I also owned. Then I realized it was Floyd wearing my sweater! I was pretty excited to see him wearing it. It made me super happy because then I knew he wasn’t just trying to wear my clothes in front of me in the beginning. He seemed like he was doing okay. He was trying to give me some math problem that had to do with the circumference of the moon, but I don’t think the question made any sense. I told him that his question made no sense and also gave him all the cash I had in my pocket, which was like eleven bucks. That was the last time I saw or talked to Floyd, but every time I pass by a black homeless dude on the street, I double check to see if it’s him.

So what did I learn from this experience?

Nothing really life changing.

It’s kind of funny how many goals I had with helping him that I never did. For example, I had day dreams about finding him a job and figuring out how he could get his teeth fixed, but I barely even found the energy to meet him up. I learned it’s super easier to just think about doing nice things than actually following through.

Even as I was writing this, I was kind of thinking about how I wished I gave him more money or something. And then I thought about e-mailing him again and immediately got lazy (but I will!).

Also, I think people just assume homeless people are homeless because they are just lazy or drug addicts, and to a degree I kind of have that view too. I mean I don’t really read up on the subject but I am pretty sure a lot of people just become homeless from circumstance. No matter how small, you’ve been privileged with a set or resources to get to where you are right now.  It’s kind of like how douchebags like Donald Trump think they earned their money when they were born into it. He claims to have started from the bottom with a “small” million dollar loan from his father. He has no perspective. So if you assume homeless people should just work hard like you, and you neglect to acknowledge, for example, how your parents supported you through high school or college, you’re kind of being like Donald Trump.

Don’t be a Donald Trump.

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