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He gives examples to illustrate his life with friends in the past and express his feelings about his life now.

He gives examples to illustrate his life with friends in the past and expresses his feelings about his life now.

In the above two sentences, the singularity or the plurality of the verb express changes the context.

I believe both are fine, just need a confirmation and/or a rule to back it up.

Is express a continuation of infinitive to illustrate or the verb of He, or could either be the case?

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    Could be either, and, as you say, the choice of verb form clarifies which it is, in this case. In many similar examples, the verb form would be the same, and the sentence is formally ambiguous. – Colin Fine Jan 17 at 8:52
  • Yes, both are fine. Syntactically, they are different and, as you say, the meanings are different. Your first example has a lengthy infinitival clause (a purpose adjunct) containing a coordination of verb phrases, as shown in brackets here: "He gives examples to [illustrate his life with friends in the past] and [express his feelings about his life now]. – BillJ Jan 17 at 8:52
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    @ZeeshanAli Colin is referring to possible ambiguity in similar sentences. See my answer below. – Tashus Jan 17 at 15:45
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    @BillJ I believe Colin means that similar sentences may have ambiguity because the two verb forms would be indistinguishable, as in the example in my answer. – Tashus Jan 17 at 15:46
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    That is indeed what I meant, @Tashus. Sorry if it wasn't clear. – Colin Fine Jan 17 at 22:11
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As you say, either word can be appropriate, and they express two different things:

He gives examples to illustrate his life with friends in the past and [to] express his feelings about his life now.

He gives examples to illustrate his life with friends in the past and [he] expresses his feelings about his life now.

The rule that clarifies the meaning is simply the form that the verb takes. However, as Colin has pointed out in the comments, similar sentences may be ambiguous. For example:

I give examples to illustrate my life with friends in the past and express my feelings about my life now.

In this sentence, "[to] express" and "[I] express" are indistinguishable. Grammatically, this sentence is ambiguous. However, the probable meaning can be understood from context. The phrases "...illustrate my life with friends in the past..." and "...express my feelings about my life now..." have an obvious parallel structure, so most native speakers would assume the "[to] express" meaning.

The ambiguity of the new example can only be resolved with complete certainty by changing the structure of the sentence, such as by including "to" or "I".

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