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I was writing a sentence with the word "help" and wanted to substitute it for the word "assist" but realized I could not do that without restructuring the sentence.

My original sentence, "I'll help you overcome the obstacle" (sentence 1), sounds fine.

But swapping out the word "help" led to: "I'll assist you overcome the obstacle" (sentence 2) which does not sound right.

I feel like it should be: "I'll assist you with overcoming the obstacle" (sentence 3), but I cannot figure out why the direct substitution (sentence 2) is incorrect when the two sentences have the exact same meaning and both "help" and "assist" are verbs? Is sentence 1 actually incorrect?

Additionally, I suppose the original sentence could also have been written as "I'll help you to overcome the obstacle," which would lead to the substitution of "I'll assist you to overcome the obstacle"; this doesn't sound as bad as sentence two but still doesn't seem quite right?

Why can't I directly interchange these words?

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    Just because one word can mean the same thing as another word does not mean that it takes the same syntactical form.
    – Jason Bassford
    Commented Nov 8, 2018 at 20:56
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    I realize this is not necessarily very assistful ;-), but it's because the verb help allows two objects: a person being helped, and an action that you are helping with; while assist only allows one object (the person being helped).
    – Hellion
    Commented Nov 8, 2018 at 21:27
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    @ Hellion That should be an answer.
    – Greybeard
    Commented Dec 16, 2022 at 11:48

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Per both the American Heritage and Merriam-Webster dictionaries, assist is typically used to mean more of a supplementary effort, while help is more of a direct action, with AH defining it as "to give assistance to; make it easier for..." and MW as "to give assistance or support to."

The difference is pretty subtle, but it helps explain why assist is usually followed by something like with... or in... . If someone offers to help me get a job, I would expect more effort on their part than if they offered to assist me in getting a job.

There's also a certain formality in both "help you to" and "assist you with." You can avoid that by just saying help, but because assisting is providing supplementary effort, in most cases you'll have to keep the with or in specifier to indicate what you're doing.

To your original sentences, the first one, "I'll help you overcome the obstacle," is an (unconditional) offer that you'll do what you can to help that fellow.

If you tell a fellow "I'll assist you with overcoming that obstacle," you're implying that that fellow must do their part in overcoming the obstacle, and you'll supplement their effort where you can.

Imagine you're on the side of a busy highway with a blown tire in the rain, and two folks stop to help. Person A offers "I'll help you change that tire," and Person B offers "I'll assist you with changing that tire." Person A's offer is a lot more direct, while Person B sounds strangely formal for the situation at hand.

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