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I think in spite of many other similar question like:

  • What / how about this plain shirt?
  • What do you think about this plain shirt? and so on.

the sentence: "How do you like this plain shirt?" implies that the question maker has a semi-positive opinion about the shirt in his / her question, but they doubt about it and need to know about the second person' opinion. Do you confirm it?

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I have to disagree. Grammatically, the sentence is doing no more and no less than asking to what extent the other person likes the shirt.

Compare: How do you like your boss?

This does not imply any favor or disfavor on the part of the person asking.


That said, practically speaking, when you ask someone about a shirt, you are typically considering buying/wearing it, and thus typically have at least a semi-positive opinion of it. But that's true of all your example sentences.

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Absolutely.

'How do you like' - is asked when you are convinced or almost convinced that sth is good / decent etc and you want to know others opinion about it. Especially you expect a positive or an appreciative response.

For example

A girl is wearing a new dress and is showing that to her boyfriend, then she would ask

How do you like my dress ? (It means she already liked it and wants his opinion.)

(This question can be asked after she bought the dress or before buying it i.e. when she wants to try it on or just showing it to her boyfriend.)

In the same way if you are a local citizen and giving a treat to your relative from the other city in a famous restaurant in your city then you might ask

  1. How do you like the food ? (When this action (eating) is in progress)
  2. How did you like the food ? (Now this action (eating) is not in progress. So you might be asking this question on the next day)
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    +1 But would like to add that this sort of simple statement is very commonly used sarcastically. ex: How do you like these new uniforms? This could mean that you like the new uniforms and are looking for affirmation, but it also could mean that you hate them and want affirmation of your hate. – Jason Patterson Dec 9 '14 at 19:05
  • @JasonPatterson - yeah that is a good point. – Leo Dec 10 '14 at 3:34

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