Paste Without Style
I agree with Buzz Anderson: “Paste-with-styling is one of the worst software inventions of all time.”
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Another reason for the confusion is that “and Match Style” really means “Without Style”.
I nearly always use “Paste and Match Style,” and most people should use it but probably don’t know about it. On the other hand, I think it usually makes sense to have the standard operation preserve as much data as possible. Apple made the opposite choice with the Finder’s Paste Exactly, although in that case you could argue that the information discarded by default is only metadata.
Pasting with or without styles is a thorny problem because, as Hockenberry notes, one typically wants different behavior in different applications. I think the problem of matching styles is one reason why many people prefer writing in plain text editors. Everything just looks right automatically.
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iClip (a clipboard recorder that's still supported) is not cool or popular any more, but it can do this as well, i.e. you can set it up to always paste as plain text and define a hot key, e.g. ctrl-V, to paste then. That way, you can easily choose whether to paste with or without the copied format, by using either cmd-V or ctrl-V.
The real problem is that 1. most folks don't appreciate the distinction between style and semantics, and 2. widespread authoring tools (I'm looking at you, MS Office) vastly exacerbate that problem by making bad styling practices easy as dirt and expressing good, clear semantics a near-impossible nightmare.
As to plain text editors, they're no solution because everyone just ends up adopting completely ad-hoc or pseudo-standard "plain text formatting" schemes to insert all the semantic information that plain text editors point-blank refuse to recognize at all.
Having worked both sides of this fence (book author, DTP operator), it drives me absolutely nuts the amount of time and effort that's wasted just because people and tools can't communicate effectively.