YOU SAID:

I think he knows when I play with him like that, and when I say it to him like that.

INTO JAPANESE

私が彼とそんな風に遊んだり、彼にそんな風に言ったりすると、彼は分かっていると思います。

BACK INTO ENGLISH

I think he knows when I play with him like that or talk to him like that.

INTO JAPANESE

私が彼とそんな風に遊んだり、話しかけたりすると、彼はそれを知っていると思います。

BACK INTO ENGLISH

I think when I play and talk to him like that, he knows it.

INTO JAPANESE

私が彼とこのように遊んだり話したりすると、彼はそれを知っていると思います。

BACK INTO ENGLISH

I think if I play and talk to him like this he knows it.

INTO JAPANESE

私がこのように彼と遊んだり話したりすれば、彼もそれを分かってくれると思います。

BACK INTO ENGLISH

I think if I play and talk to him like this, he will understand.

INTO JAPANESE

こうやって遊んで話せば、彼も理解してくれると思います。

BACK INTO ENGLISH

I think if we play and talk like this, he will understand.

INTO JAPANESE

こうやって遊んだり話したりすれば、彼も理解してくれると思います。

BACK INTO ENGLISH

I think if we play and talk like this, he will understand.