How to stop telling forgettable stories.

Today, Friday, February 6th, I have a story to tell you.

On my way out of MUNI this morning, I walked past a homeless man playing acoustic guitar. I was relatively tired, a little out of it, but I liked the song he was playing. He was doing alright for himself. There were a couple dollars in his open case. I walked on by and out into the fresh Financial District air.

Did I already lose you? I should have. Unless you’re in a relationship where you and your love tell meal details down to the side of mashed potatoes, no I didn’t feel like gravy, then you’re probably not accustomed to purposeless stories like this.

As an entertainer, I find the opportunity to tell a story a privilege. You should too. The story I just told you is true but worthless as is. Here are improv-based storytelling musts to keep in mind the next time you have an audience.

Meaningful details make us care

My pre-MUNI Friday morning went pretty awry. Unprepared for even a rain shower, I got poured on while it thundered and lightninged at my stop. Shoulder to shoulder in a packed car, soaked and late, I was not in the mood to appreciate art.

This homeless man, though, when I walked up, gave me a full-toothed grin mid-chorus of The Cure’s “Friday I’m in Love” (I don’t care if Monday’s blue, Tuesday’s gray and Wednesday too, Thursday I don’t care about you, Friday I’m in love). His voice was rich and syrupy, and I thought, “This man knows The Cure?!” I immediately snapped out of my crummy mood.

No stakes, no attention

When was the last time you made it through a book with low stakes? A book where, if James Wonder-Man didn’t make it to the school bus on time, a crew of fire fighters was waiting to rescue the kids anyways? No, the stakes don’t always have to be death, saving the world, or losing love for good, but we need something. 

I lied to you a little bit earlier on. Truth is, I had already started to snap out of my mood. There was a pretty girl on MUNI sitting directly across from me for eight stops. A damp, smelly MUNI is never the opening scene of a romantic comedy, but maybe just this once? At one point around Van Ness, we very clearly caught each other looking and smiled. That’s already further than most MUNI love interests go. If we got off at the same stop, I told myself, I’d break the iron-clad social norms of public transport and strike up a conversation.

Here, we at least have the stakes of stranger rejection in public.

Something has to happen, and timing matters.

If I continued to say, “So, she got off at Montgomery and I said she was pretty, ‘Could we grab coffee sometime?’ and she said, ‘No, thanks,'” then I missed out on a big opportunity. Not just with her, but in telling my story.

Generally, nothing in life worth talking about comes easily. We are programmed to care more about the well-earned payoff than the “simple as that” success story.

Really, she got off at Montgomery like me, but I started having doubts. She turned left, I turned right, and that was that. It was time to move on. I was still cold and wet, so I chose the long staircase instead of the escalator to get to station level and back to my normal rainy life.

Lo! Look who doubled back, chose the escalator and actually passed me NASCAR style in the outside lane: MUNI girl. Better yet, we were definitely headed to the same exit. My palms got sweaty like they do when I dare myself. She’s well dressed, confident, in no apparent rush. My brain is seesawing between courage and cowardice.

That’s when The Cure came on, filling the tunnel with a sound even fuller than the singer’s smile. I was almost shoulder to shoulder with MUNI girl when WOAH, she drops $5 in his case and stops in her tracks to listen to him. Everyone else is passing by. Do I stop?

Stories are the .01% of our lives

Even if I asked this MUNI girl out, and even if she said yes, and we had a nice time over coffee, etc, this story probably wouldn’t make my memoirs. If I didn’t strike up a conversation, then I probably wouldn’t tell anyone but my journal.

But if on a romantic whim, I stopped beside her and silently listened to a homeless man’s soulful rendition of Friday I’m in Love, and we knew without saying a word that this was right, and I asked her on a second date, because “that was our first,” and now that same woman is marrying me tomorrow (yes, I sound like Ted from How I Met Your Mother in this story), then this suddenly becomes a tearful speech at my rehearsal dinner.

We consume stories – books, movies, shows – to hear about that .01% of life that breaks the norm. Out of 100 girls on MUNI that I think are pretty, I probably will talk to one of them. Out of that one, there’s probably a 1% chance it will become something.

If you’re planning a big speech, scrutinize your experiences. Don’t settle for the first experience that comes to mind. Ask yourself, “Does this story shatter the norm?”

Once you’ve settled on that experience, interrogate yourself: “What details mattered to me then?” The Cure song is only worth sharing if it gave me courage to act, or if it’s still a meaningful song to this day, but not if it was just a good song. Keep the details that matter, and please take out those that don’t. The scarce, powerful, rich details will make your story stick, but too many of them are a real bore.

Full disclosure: I didn’t ask the MUNI girl out this morning, but the homeless man’s cover was truly one of a kind.

Chris Severn delivers corporate trainings through improv comedy techniques for organizations in the Bay Area. Visit to schedule a class.