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Harry kept quiet. He did not want to express the doubts and uncertainties about Dumbledore that had riddled him for months now.

Harry Potter and the Deathly Hallows

I feel 'riddle' here is used metaphorically, because I don't expect it would pierce Harry with numerous holes. What does 'riddle' mean exactly?

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    There are two definitions of "riddle", the one you found doesn't apply in this context, as you have noticed xD
    – user57928
    Commented Dec 18, 2019 at 5:20

3 Answers 3

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Contrary to most answers here, I think there are mutiple meanings here.

Doubts about Dumbledore had riddled him

You could argue (as others have) that the doubts he had about Dumbledore were puzzling to Harry.

However, unless Dumbledore actually set him some riddles/puzzles to solve, I think it really means that Harry is:

Riddled with doubt

This is a metaphorical usage of being filled with something - This implies that he had many doubts and uncertainties that he was struggling with.

See Merriam Webster definition of riddle:

3: to spread through :
permeate a book riddled with errors

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    This is the best answer; the use of "riddled" with "doubt" certainly invokes this idiom, and the sentence definitely reads either way.
    – BadZen
    Commented Dec 18, 2019 at 13:31
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    To me it seems unambiguous if I pay attention: It's not "Dumbledore that had riddled him" - it's "the doubts that had riddled him" where the doubts are about Dumbledore.
    – Criticizing Israel not allowed
    Commented Dec 18, 2019 at 15:23
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    As a native speaker of British English, this is my instinctive reading of the sentence. I notice that most of the answers disagreeing with this appear to be from speakers of American English - as such, I wonder if "riddled with doubt" is an idiom less familiar in the USA?
    – Chronocidal
    Commented Dec 18, 2019 at 16:15
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    I strongly suspect, as Chronocidal's comment implies, that the answers that give the puzzle definition were written by people not familiar with the idiom. As a native AmE speaker, I also echo BadZen's that it is a well known idiom AmE too.
    – weissj
    Commented Dec 18, 2019 at 18:24
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    @BadZen Given the importance of the name Riddle in the story, how can we not read it as a pun?
    – Anton Sherwood
    Commented Dec 18, 2019 at 20:54
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The noun "riddle" is a kind of verbal puzzle, and there is a corresponding verb with the primary meaning of posing such a puzzle. So there is no reference here to the verb "riddle" with the meaning of "pierce." Instead, the meaning is simply that doubts had puzzled Harry. In my part of the U.S., this usage of "riddle" as a verb where a situation rather than a human is the riddler is rare enough to be quite odd, but it may be common elsewhere. Nevertheless, the usage would be comprehensible to almost any native speaker.

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    There is a reference to the idiom "riddled with doubt", which does not imply "puzzled".
    – BadZen
    Commented Dec 18, 2019 at 13:29
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    "doubts had puzzled Harry" - this essentially means Harry is confused, which he is. Can someone explain the downvotes? I don't get how this answer is soooo outrageous to merit 3 downvotes. Since when have we started to downvote less than perfect answers? Is this answer perfect? No. Is it wrong? No. Is it partially correct and useful? Yes. If you hover over the downvote arrow, it says "this answer is not useful". It is useful. The highly upvoted answer also says this is one meaning. I honestly don't get it. But I want to hear and understand why this answer is so bad.
    – AIQ
    Commented Dec 18, 2019 at 20:52
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    @AIQ Is it wrong? Yes. Refer to Smock's answer which references Merriam-Webster.
    – Adeptus
    Commented Dec 19, 2019 at 4:16
  • @Adeptus To me both answers are pointing out the same thing. Smock's answer just does it in a better way. Can you tell me which part in Jeff's answer is wrong? Smock's answer cover Jeff's answer too.
    – AIQ
    Commented Dec 19, 2019 at 4:19
  • Jeff says it means "puzzle". The pertinent part of Smock's answer says it means "filled with" or "spread through", which arises from the same root meaning as "pierced" - a riddle being a sieve; being riddled with holes; being riddled with <something else>.
    – Adeptus
    Commented Dec 19, 2019 at 4:28
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True! It's in the sense of puzzling the character.

Check the verb version here in this dictionary -

A question or statement requiring thought to answer or understand; a conundrum.

It's an entry for v. rid·dled, rid·dling, rid·dles

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