Is the pastel purple covering grey or white hair, or just a skilful dye job? Is their hat cringe or back in fashion? Do the number of piercings make a difference any more?

And having too many similar sounds also plays a part. Matthew Andrew flows nicely, but the vowel sounds are too similar so it is a little off. Matthew Edward works better

It's a fun game to give people new middle names and call them by it. Especially if they didn't have one to begin with

Christopher Robin sounds much better than Chris Robin, or Robin Christopher, because it almost bounces from the last syllable and flows into the middle name.

It also can differ if you shorten a name. A middle name that works after Sam may not work after Samuel. Or shortening a middle name just feels very wrong. Samuel Edward yes. Sam Edward yes. Samuel Ed? Crimes.

It's mostly about the rhythm. A balance of long and short names, but there is also how the names flow into each other as you say them, which is probably affected by accents and different languages

I would fight anyone who says a bad word against Dimbleby

I have been managing a citation library for work, and some of the authors make me chuckle every time:
Carnevale, C (followed by Carny, E)
Casanova, M
Cupples, L
Dimbleby, G
Ding (followed by Dong)
Godbehere, J
Hogsbro, M
Pickles, J
Yawn, R