Dr. Leslie Berkowitz

Dr. Leslie Berkowitz is the physician Penelope works for, a well-meaning boss whose small talk tends to veer into oversharing and mild chaos. He means well, dispenses advice nobody asked for, and treats the office like an extension of his own anxious inner monologue. Harmless, odd, and oddly endearing.

Tobolowsky plays him with a specific brand of nervous, run-on earnestness that turns throwaway scenes into comic set pieces — he can make a routine check-in feel like a confession booth. The show uses him sparingly but precisely, letting his oddness puncture heavier moments with exactly the right amount of relief.