I play for a number of older residents. I try to keep the music light and fun as a number of folks are prone to sadness/depression.
My wife and I have many favorite tunes that speak of one partner gone and the other left behind.
Two in particular are If You Get There Before I do and Far side Banks of Jordan.
However we have, at times, seen tears of sadness, folks missing a loved one, when we do these songs.
So we try to do these types of songs judiciously only when we think they might give hope or cheer rather than depress.