All the things Schmidt has built through his life time, his career, his family, becomes loose, especially after his retirement and his wife passes away. The company he has worked for dozens of years doesn't appreciate his work any more when young managers take over his position. His daughter has her own relationship troubles going on and doesn't listen to his advice on her marriage. She is no more as close to him as in her childhood. It looks like that he is no more useful to any other people around him. Thus Schimidt seeks for a place where he can make the connection. So he goes to visit his birthplace and his mother school. But this is so miserable, as he only can make connection with the past instead of the present. Because everyone has the past and it's not anything hard to connect with.
That's why it's funny when he encounters a stranger who says that she can tell his deep emotions, he couldn't help himself foolishly throwing trust and presenting the need for being cared on the random woman. It is temporary sentiment that easily occurs to other old and lonely people. For example, the groom's mother who's just so open about sex topic at the first sight of him.
It is misery. A misery in comedy way.
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