So sad did she look that I didn't know what to say to comfort her.

她看起来很伤心，我不知道该说什么来安慰她。

youdao

I only know that falling in love should be the happiest time of your life. You seemed so sad.

我只知道，恋爱应该是你生活中最快乐的时候。可是你似乎很伤心。

youdao

You know I don’t think I was quite as sad as that, albeit maybe I was and he perceived that and I didn’t.

你知道，我不认为我是那么伤感的，尽管我可能而且他察觉到我是，但我没有那么伤感。

youdao

"I'm sad because I know that somebody hurts and somebody grieves, somebody's heart is broken, " he said.

CNN: Bush in Ohio defends war

The sad part is that after 5 years, I still know people (builders, electricians, carpenters) waiting for things to get back to normal.

FORBES: Cities Where Home Prices Are Still Tumbling

Mr. BEYER: Well, this was - this was as, you know, sad a day at the racetrack as I've spent in my life, and that encompasses a lot of days.

NPR: Heartbreak at the Preakness Stakes