I decided to do something pretty random to give away $100 today. I was driving home down 15th Avenue and saw a man sitting in a bus shelter. I had the impulse to pull over but it was too late; traffic was heavy and I kind of got swept along. I got the idea to stop for the next person I saw waiting for a bus. I made it all the way down to Fremont St, where I saw a man standing at the stop. I pulled into the Whole Foods parking lot and was just getting out of the car when the bus pulled up. Dang! I had barely even seem him but there was something I liked about that guy.

Missed my chance with guy #1

It was pretty cold out so I sat in the car for a few minutes, keeping my eyes on the bus shelter. It stayed empty. I decided to make a quick run into the store.

A couple of grapefruits and oranges in hand, I was back outside in a few minutes. I saw a young woman sitting on  the bench, her head bent down. I marched right up to her, all pleased with my plan.

“Hi, how you doing?” I asked. “Good,” she said, looking at me somewhat skeptically. Then she gave me a slow smile. “It’s chilly out here.” “Yeah, it is,” I agreed. I told her I was paying forward a gift and had decided to give it the next person to come to the bus stop. “Oh, I’m excited!” she said.

I held out the C-note. “I hope this makes your day even better,” I said. “Oh, wow,” she said as her hand closed around it. Then she looked at it fully. “Oh, my gosh! Really? Thank you so much!”

She told me her name was Caitlin and she had just moved out of her parents’ house to live on her own with a friend. “This will really help, so much! For groceries, whatever!” She wanted to know why I had decided to give the money away. When I told her that my mother had died she put her hand over her heart and said how sorry she was. She’s finishing her studies in psychology and hopes to get a job teaching special needs children.


I told Caitlin about the blog, then she thanked me again and we shook hands and said goodbye. When I got back to my car I could see her talking on the phone, smiling and smiling. I hoped she was telling a friend about her random good fortune. You just never know what might happen in this world.

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4 Responses to Caitlin On Her Way

  1. […] This post was mentioned on Twitter by Courtney Boell, hundredsof100s. hundredsof100s said: I decided to give away $100 today; pretty random. Read latest post on Hundreds of Hundreds blog: Caitlin on Her Way http://bit.ly/eLyR9o […]

  2. Pru McDonald says:

    With a generous stranger like you loose in this world, yes! Anything can happen! How wonderful for Caitlin, and how doubly wonderful for YOU, Jill!
    How gratifying it must be to know that you have made such a HUGE difference is someone’s life with those magical C-notes! Haleluja! Pru

  3. DJan says:

    It’s not really the money but the recognition and the random connections, to me anyway. I love the stories of people who are recipients of your largesse. What a way to make a difference in someone’s day…

  4. Carrie says:

    Seriously, all of your stories make me cry. Very touching! This one was so simple… But I bet a hundred dollars made a huge difference to that girl!

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