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似てるよ、ユーマくんと初めて出会って時と。

I'm slightly confused at how と is used at the end.

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First, I think it is supposed to be 出会った時, not 出会って.

Second, it will be easier to understand if you invert the sentence:

ユーマくんと初めて出会った時似てるよ。

It's similar to that time when I first met Yuuma.

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