I'll have steak tartare before I'll eat a rare steak. Either cook it or don't.
Some cuts, like sirloin, are good at medium-rare, many others are better at medium.
A good fatty ribeye can be cooked as much as medium-well.
Preferring well-done steak is either a sign of past trauma (like food poisoning) or is a serious character flaw.
Bob probably cut into the steak before it had sufficient time for the heat to finish the carryover cooking.
Always remember to rest your meat!