Matt talks about the two main ways we use the word "sad." It can be used as a feeling of unhappiness, but also as an insult for a situation or person that is unaccomplished or pathetic.
Examples:
-I am sad to hear that you are leaving.
-She looked sad when I told her the news.
-Does that make you feel sad?
-That was a sad showing from the local sports team.
-A: Did you see that guy fail? B: Yeah, that was pretty sad.