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The dictionary says

pay somebody to do something

Ray paid some kids to wash the car.

However, they didn't explain how to use this structure pay somebody to do something correctly.

Is it confusing to say "I paid him 20 dollars to buy the T-shirt"?

That is because "I would buy the T-shirt" or "He would buy the T-shirt".

It could mean I was lazy to buy the T-shirt so I asked him to buy it for me and I would pay him $20 for that.

It could mean I bought the T-shirt from him for $20.

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    It's confusing. "I gave him $20 so that he could buy the T shirt for me" would be clearer.
    – Maths Barry
    Commented Aug 30, 2022 at 7:04
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    Tom, the simple present of action verbs is used for general statements. So, you need the continuous: "I'm paying him 20 bucks to [etc.]". In any case, your question is not really grammar.
    – Lambie
    Commented Aug 30, 2022 at 14:54
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    No, "I paid him 20 dollars to buy the T-shirt" does not and cannot mean that you bought the T-Shirt from him for $20. There is no implications of laziness, but it does indeed mean that you literally paid him 20 dollars to purchase the T-shirt. This statement has 2 additional implication's which may not be true: that you supplied additional funds for the actual purchase, and that the shirt would be handled over to you afterwards. Neither are hard requirements, you might not have provided additional funds and he might have kept it for instance (you paid him $20 to buy himself a gift).
    – jmoreno
    Commented Aug 30, 2022 at 17:26
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    @jmoreno It can mean that - with "to" meaning "[in order] to". Consider "He was asking for 15 dollars for the shirt, but I paid him 20 dollars to be generous". In isolation, the interpretation of "[in order] to" isn't the most likely interpretation, but it's definitely not out of the question.
    – Deusovi
    Commented Aug 30, 2022 at 18:05
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    to pay X to buy sounds odd and redundant for most casual conversations. In most situations nobody would actually talk like that and that would be one clue to consider the second meaning.
    – shawnt00
    Commented Aug 30, 2022 at 18:49

4 Answers 4

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I agree with you that

"I paid him 20 dollars to buy the T-shirt."

would most likely mean that you asked him to buy it for you.

If you instead are buying it from him, it would make more sense to say

"I paid him 20 dollars for the T-shirt."

or even better

"I paid 20 dollars for the T-shirt."

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    If I meant I were sending him to buy the shirt, I would probably say, “I gave him twenty dollars to buy me the T-shirt.”
    – Davislor
    Commented Aug 30, 2022 at 16:21
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    This one's fun to play with. "I paid 20 dollars to buy the T-shirt" (omitting "him") and "to buy the T-shirt, I paid him 20 dollars" also seem to mean that I personally bought the T-shirt, even though "to buy" is still in each sentence.
    – TylerW
    Commented Aug 30, 2022 at 21:36
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    Agree with @Davislor, the use of "paid" implies the person is gaining money in exchange for something - they are somehow earning $20, and it's oddly implied that they are earning it by buying the shirt. A more common parallel phrase would be "I paid him $20 to mow the lawn," meaning that I gave someone $20 in exchange for a service. "I paid him $20 to buy the shirt" is very unclear as to whether that person is earning $20 by buying the shirt, or if they're just given $20 to buy a $20 shirt, or what exactly is happening.
    – Nuclear Hoagie
    Commented Aug 31, 2022 at 15:23
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    I disagree that the last one is "even better." It loses the information of who the shirt is purchased from.
    – Michael Mior
    Commented Aug 31, 2022 at 19:04
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    I think it's a stretch to say that dropping "him" in "I him paid 20 dollars for the T-shirt" is "even better". It removes detail from the sentence that may be important.
    – Shadow
    Commented Sep 1, 2022 at 4:49
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Yes, that is confusing, because what it literally says is very unusual. You would probably consider this an error for the more common sense.

It literally says "I gave the man 20 dollars, in exchange, he bought the t-shirt" It would be odd, but I suppose you could imagine an exchange like:

Oh my goodness, look at that ugly t-shirt! It is the worst I've ever seen.

It's only five dollars. I dare you to buy it.

But don't want such an ugly t-shirt.

I'll pay you $20 to buy the t-shirt. Come on, it will be funny.

Or I suppose your example with the lazy man is also possible.

Can you buy me a t-shirt, I'm too lazy to go to the shops. Here's $45 for the t-shirt and I'll pay you $20 to buy the t-shirt for me.

All very unlike situations. Normally you buy clothes yourself, and you'd say

I paid $20 for the t-shirt.

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    Here is a situation where the sentence makes good sense: imagine that you wish to acquire the T-shirt of Nessus, presumably to dispose of an enemy. Since you don't want the shop assistant to remember you, you find someone who doesn't look like you, and pay him to buy the T-shirt.
    – Simon Crase
    Commented Sep 1, 2022 at 3:31
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To pay someone means to remunerate (compensate for, make payment for) someone, such as for a service rendered.

Saying that you paid someone to buy a shirt sounds like you gave them money to keep for the service of buying the shirt. What I think you mean to say is that you simply gave them the money so that they could buy it on your behalf.

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The T-shirt is sold in a store, for some amount, say $12. Of the $20 you've given your friend, $12 will go to the store, and $8 will go to your friend. You can say:

  • Your friend has received an $8 commission to buy a $12 T-shirt for you;
  • You gave your friend $20 to buy you a T-shirt, and told them to keep the change.

The second one is probably more accurate because you don't need to know how much the T-shirt was sold for; in fact, your friend might have had to make a choice, for instance between a $10 T-shirt at a far-away shop or a $14 T-shirt at a close shop. The choice is theirs and you don't care either way, since you always end up paying a total of $20.

If you say "I paid my friend $20 to buy a T-shirt", it's pretty confusing, because it sounds like those $20 will all go to your friend, and do not include the price of the T-shirt.

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  • When writing dollar amounts, the dollar sign always precedes the number. You write $10 but say "ten dollars". The same is true of pounds and euros, when writing in English.
    – James K
    Commented Sep 1, 2022 at 10:33
  • @JamesK Indeed! Thank you
    – Stef
    Commented Sep 1, 2022 at 10:35

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