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When writing a sequence of actions that happen after each other I get regularly confused about the correct use of the present participle. For example in:

A: I prefer learning by gaining an overview first and then deepen the understanding of the details.

B: I prefer learning by gaining an overview first and then deepening the understanding of the details.

C: I prefer learning by gaining an overview first and by then deepening the understanding of the details.

I’m not sure which grammatical rules should exactly be used here.

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    Prefer is an implicit comparative: X prefers Y to Z means that X likes Y better than X likes Z. Comparatives have two parallel clauses; if you use a gerund in one, you should use a gerund in the other. So the second case is preferred, while the first case, as stated, is ungrammatical. – John Lawler Aug 28 '13 at 23:40
  • @JohnLawler As I understand your explanation, the two parallel clauses refer to the clause Y is parallel to the clause Z. But, in the examples given there are no "Z-parts", since no explicit comparisons are made. So how does your reasoning apply to the above then? – alexlo Aug 28 '13 at 23:48
  • @JohnLawler Isn’t there a more general rule than the implicit comparative? To me it seems that this construction "… by V1 first and then V2" could be used elsewhere too. (By the way, I edited the question a little bit, in case you responded to an old version.) – Lenar Hoyt Aug 28 '13 at 23:49
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    Sure; you don't have to even refer to the comparative. I overcomplicated it. Neil got it right below. Good on him. – John Lawler Aug 29 '13 at 0:32
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    @mcb It says that most of us avoid using the same form twice in a row; I think what it really represents is that we avoid using identical forms when they falsely suggest syntactic parallelism. – StoneyB on hiatus Aug 29 '13 at 10:33
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In general(*), if the complement of a verb/preposition is an -ing form, then when coordinating that verb, native speakers will coordinate it with another -ing form. So (A) and (B) have different interpretations:

(A) I [prefer...] and then [deepen...]

(B) I prefer [ [learning...] and then [deepending...] ]

In other words, in (A), it is implied that 'prefer' and 'deepen' are separate actions, whereas in (B), 'learning...' and 'deepening...' are portrayed as the things you prefer (or, collectively, the sequence of events you prefer).

Your version (C) is grammatical, but sounds a bit clumsy.

(*) There are interesting exceptions to the 'like coordinates with like' pattern that I won't go into here.

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