As a bit of background, my grandfather is named Lester Leary. My father is Brian Lester Leary. I was named Seth Lester Leary. Because of the recurrence of the name Lester I took the liberty of calling myself "the Third" (III). Following this pattern, I named my first son Jared Lester Leary IV (the first "legal" instance of this enumeration).
Today Jared asked me if he would get to name kids (presumably his own). I told him he would. He then asked if he could name one "Lester the Fifth." I chuckled and said that he could, and that I would be very pleased if he did so.
It's funny, because even though I had the intention of naming him "the Fourth" long before he was conceived, I had honestly never thought of the pattern continuing beyond that until this very moment. I'm glad he has already embraced his unconventional name as an honor, rather than an mocking punishment.