YOU SAID:

My little brother likes studying and likes making me cry.

INTO JAPANESE

私の弟は勉強が好きで、私を泣かせるのが好きです。

BACK INTO ENGLISH

My brother likes studying and makes me cry.

INTO JAPANESE

兄は勉強が好きで、私を泣かせます。

BACK INTO ENGLISH

My brother likes studying and makes me cry.