YOU SAID:

I wish I could have spent more time talking to my friend tonight.

INTO JAPANESE

今夜、友達ともっと時間をかけて話せたらよかったのに。

BACK INTO ENGLISH

I wish I could spend more time talking with my friends tonight.

INTO JAPANESE

今夜は友達ともっと時間をかけて話ができたらいいのにと思います。