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Context: some guys are beating up a high-school girl to extort money from her. Then she says(in a defiant tone I think):

今時かつあげ?チャラいわりにやるコトは古いのね

I checked this question about チャラ, but I didn't find a meaning that fits the context. Also, I am not sure about the actual meaning of わり here. Thank you for your help!

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...わりに means "for ..." or "considering ..." as in "You look young for your age". So basically the girls is saying "Ha, you're doing an old thing in spite of your チャラい appearance."

This means she believes カツアゲ is an outdated act, and チャラい people do not usually commit カツアゲ. Well, I also think this is a general tendency.

In school dramas/manga, カツアゲ is usually considered as a delinquent action committed by people like this:

硬派

This is a stereotype which is typically referred to as 昭和の硬派な不良 (lit. "Hard-faction delinquent of the Showa era") today. They are characterized by stubbornness, dignity, violence, hierarchical relationships and resistance to adults. This type of 硬派な不良 is almost dead now, but the word カツアゲ is still associated with this type of school boys.

Today, the word チャラい refers to the opposite of this, characterized by talkativeness, frivolousness, women-chasing, opportunism, sensitivity to fashion/music, and fast-living attitudes. The antonym for 硬派 was 軟派, but it came to mean "to pick up a girl", and today チャラい (i-adjective) has become widespread. (Of course the actual appearance of 軟派/チャラい people will vary from time to time; no one looked like Fujimori Shingo 40 years ago.) While チャラい people may be generally considered by many to be superficial and lacking patience, they seldom take a risk and resort to brute force.

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I think here you should actually look at わりに, that means rather/fairly etc. You can look it up here.

In case you have AわりにB, usually this means that B does not meat the expectations of A. So in this case I think a possible (free) translation would be:

You extort money now? Quite an obsolete move for a charai. (Or similarly: For being charai that's quite an old/outdated move)

I left on purpose "charai" in Japanese as it could have different meanings depending on the context, but usually it's used as "playboy/player".

So my first idea was that the girl could be trying to get back at them by saying that they are using an outdated move to hit on her.

EDIT: However, as pointed out in a comment, チャラい has a connotation of "being easily affected by fashion" or "hip", and so the contrast is in the fact that extorting money is outdated for someone who looks fashionable.

I think I might have been misled by the context that maybe was not clear enough. So maybe a more correct translation (always free) would be:

Extortion? So outdated for someone who tries to/wants to look so fashionable.

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    チャラい itself is an i-adjective meaning frivolous. チャラい has a connotation of "being easily affected by fashion" or "hip", so the point is カツアゲ looks old while you look fashionable. – naruto Apr 11 '17 at 2:04
  • Well maybe the context wasn't clear enough. What is in the context that makes my interpretation wrong? @naruto Anyway I edited the answer after your comment. Do you think it's more clear now? – Tommy Apr 11 '17 at 2:19
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    I don't know the direct equivalent of チャラい, but it is not really a positive word. "Someone who (at least) tries to look fashionable" or something sarcastic might be better. – naruto Apr 11 '17 at 3:10
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    @Tommy sorry if the context wasn't clear enough. I don't think they are trying to hit on her, because they're beating her up really badly, they are actually threatening her life to extort her money. – Marco Apr 11 '17 at 7:46
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    Anyway the whole point of my answer was to point out that you should have parsed わりに as a whole. :) – Tommy Apr 11 '17 at 8:30

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