This happened in Jacksonville years before I moved back here.
I was working for ACTS 29 Ministries, so it was probably around 2000. My stepdad was president of the ministry, and he was leading a conference at Redeemer Episcopal Church.
I had recently met Paul and Lisa Bryan, who were close friends of my parents and big supporters of the ministry. I remembered—or thought I remembered—my mother telling me that Lisa was bringing her daughter to the event.
You can probably already see where this is going.
Lisa showed up with another woman, and I decided I was going to be friendly and engaging. I introduced myself and told the woman how nice it was to meet Lisa’s daughter.
Big mistake.
Lisa looked at me and said, “It’s nice to see you, too, Doug. And this isn’t my daughter. It’s my best friend. And we’re the same age.”
Horrors.
In one sentence, I had made Lisa about 25 years older and her best friend about 25 years younger. One of them had just received a wonderful compliment.
It was not Lisa.
I immediately started looking for the biggest rock in Jacksonville so I could crawl under it. I spent the rest of the weekend avoiding eye contact with her, which probably made the whole thing even more obvious.
Every time I saw Lisa after that, one or both of us would bring it up. Some embarrassing moments fade with time. Others become part of your permanent record.
I’ve since learned not to try quite so hard to be charming and engaging. Sometimes it’s better to let people introduce themselves before you start guessing ages, relationships or where they belong on the family tree.
The old saying about assuming isn’t always true, but in this case it was at least half right: When we assume, we make an ass out of you and me.
There was only one ass in that conversation.
It was me.
Enjoyed this? Subscribe and get future reflections, bourbon notes, and assorted nonsense delivered straight to your inbox.
Copyright © 2026 Doug DeBolt.
