Once upon a time I used to read all python-dev posts and bugs.python.org issues, so I got to follow (and get a feeling of knowing) these people I admired working and discussing together. Tim was always a favorite.

Another thing that made me feel close to him was his work on the Python Cookbook 2nd Edition, in which he (and other big names in the community) delightfully talks the reader through intricacies and insights of programming, "We read Knuth so you don't have to".

Watching Tim do his thing was a pleasure. He'd go from long, deep technical dives (that he'd make as approachable as possible) into comic relief and human connection in the fractional wink of an eye.

The brief interactions we had will always be cherished as high points in my Pythonista trajectory.

One favorite of mine was this response: https://www.python.org/doc/humor/#id15. I also like https://www.python.org/doc/humor/#id19 very much.