> どうしても入り方にこだわりたいのか...

I'd like to know how 方に works here. I don't think it's read 入{はい}り方{がた}, 'time
of setting', given the context I have. More likely it's 入り + 方に, since in the
story the speaker seems be coerced into entering some kind of contest.

I found [an example on
Tatoeba.org](http://tatoeba.org/eng/sentences/show/107532) of 方{ほう}に
translated as 'made for':

> 彼{かれ}は戸口{とぐち}の方{ほう}に進{すす}んだ  
>  'He made for the door'

Maybe that use of 方に could fit into the sentence in question...
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particles
Use of 方に In this sentence
Pretty sure it's `入{い}り方{かた}`, which here means "way/means of entering [the
contest]". And `こだわる` here is probably "insist on, make fuss about". So, I get
something like:

"Do you really want to get me into that contest no matter what?"

Check a grammar book about the [`～方`
suffix](https://japanese.stackexchange.com/questions/6823/).
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First of all, 「入り方」 is read 「はいりかた」 --「 **か** た」, not 「 **が** た」. It means
"how to 入る".

Although OP has not provided enough context, I am going to jump the gun and
post an answer.

「入る」 here looks like it is being used for its slang meaning of "to start a
performance". It is used rather heavily in show biz since many performers
think the beginning part is important for the success of the rest of their
performance.

「～～にこだわる」 means "to stick to one's way of doing ~~".

Thus, the sentence in question would mean:

"Do you absolutely have to (or "want to") stick to your own way of starting
your performance?"
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