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I know that 別に means "not particularly" sometimes, but what is its role in this sentence?

別に山田の私服を見るのは、はじめてってわけじゃないんだけどな。

I assume it means something like "it's not exactly the first time I've seen Yamada in plain clothes", but I don't know what exactly 別に is doing or what verb it's modifying.

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 Certainly. The definition given in 大辞林 is below.

( 副 ) (下に打ち消しの語を伴って)取り立てて言うこともないという気持ちを表す。とりたてて。特別に。 「 -用はありません」 「 -変わった様子もない」 〔その話題を軽く拒否する気持ちを表す。応答の言葉として,感動詞的にも用いられる。「『寒くないか』 『-』」〕

So as you said, "not necessarily need to mention 〜", "It goes so particularly without saying..." etc?

And what it modifies is the postpositional particle ぬ or ない, which denotes the denial of the noun, noun phrase, adjective, etc, which comes "before" ぬ or ない。

Ex : 今日は別に寒くない。--> Today, it is not cold especially.

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