Meaning of 性懲りも無く頭を過ぎった

Question

I started translating a manga to get a better real world grasp of the language. I also have the english version to help me cross check my translations. But the following sentence is giving me a hard time and doesn't match the english version at all (from what I can tell):

性懲りも無く頭を過ぎった

Edit: The same "box" from the english version (usually it matches perfectly):

I wondered if this person might want to be my friend.

I found this text at another location. (Web Novel vs Light Novel but 99% matching) This could be the corresponding translation: I often wished I could find someone like that.

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What I gathered so far with the help of Google translate and weblio.jp:

性懲り -> discipline

無く -> without

頭 -> head

過ぎる / 過ぎった -> pass / passed

Full Google translate is I passed my head without discipline which doesn't make any sense here.

Context: Person A meets Person B but is afraid of people and wants to chase her away at first. But what she really thinks is that she wants to make friends and talk to people.

From the manga ぼっち怪物と盲目少女

What is the meaning of this sentence?

Answer 1

First of all, please forget the "matching" translations you found. You're somehow seeing something totally irrelevant.

性懲り on its own means something like "learning (by a bad experience)" or "feeling like not repeating something any more". But this word is used almost exclusively in the idiom 性懲りもなく ("without 性懲り"), which you should learn as a set phrase.

性懲りもなく means something negative like "as if [one] had forgotten the lesson (learned by a bad experience)", "like someone who does not learn by mistakes", "doggedly", "yet again", etc.

頭を過ぎる【よぎる】 is another idiom meaning "to cross one's mind" or "to come to mind".

Thus 性懲りも無く頭を過ぎった means "[Some idea] persistently crossed my mind" or "It came to my mind yet again". The nuance is that he already learned it's a bad idea, but somehow cannot get rid of it.

Answer 2

So this is the original context:

I must say in the beginning that the sequence 性懲りも無く頭を過ぎった would be hard to make sense if there were no specific context, though both 性懲りも無く and 頭を過ぎる are common idioms (see @naruto's answer).

The main reason is that this expression is a transferred epithet which is not conventional. 性懲りも無く "despite one's failures" should obviously depict a person, but what 頭を過ぎる "cross the mind" is an idea.

With rhetoric torn away, it seems to mean "even though I have experienced numerous letdowns, it popped into my head (again)". The English translation you saw looks like a part of a paraphrase rather than a faithful one.

As an aside,

この時　性懲りも無く頭を過ぎった　「この人なら友達になってくれるかも」と

is the full continuation of sentence here. It is inverted and grammatically unmatched, but somewhat obscured by fragmentation and interruption of other balloons. A consistent sentence would be:

この時、「この人なら友達になってくれるかも」という考えが性懲りも無く頭を過ぎった。