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Today, while I was watching a video on YouTube, I came across the following sentence:

Contrary to my personality, my sister is very outgoing and tends to make friends easily.

From a meticulous academic writing view, I feel there is something off about the comparison that is established in the sentence: the two elements that are being compared to each other are my personality and my sister which doesn't make any sense. Thus, if I were to write this sentence, I would reconstruct it by adjusting either of the two elements:

  • Contrary to my personality, that of my sister is very outgoing and she always tends to make friends easily. (I am not totally satisfied with this one. Just trying)

  • Contrary to myself, my sister is very outgoing and tends to make friends easily

Can anyone clarify it a little bit and distinguish right from wrong?

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    Your observation is correct. I would express this as Unlike me, my sister is very outgoing and tends to make friends easily. – Davo May 10 '17 at 18:41
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Although the original sentence may make sense or be accepted in everyday conversation, you are right; it does not entirely make sense.

Contrary to my personality, that of my sister is very outgoing and she always tends to make friends easily.

The above sentence is much better, except for the fact that it seems you have forgotten the comma after outgoing to separate the two complete sentences. Otherwise, the sentence appears correct.

Contrary to myself, my sister is very outgoing and tends to make friends easily.

This sentence works, too, but, because it is acting neither as an intensive pronoun nor as a reflexive pronoun, myself is not necessary and would actually be considered grammatically incorrect to many linguists (but I can see why you put that since it does add emphasis); Contrary to me would be a better option.

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