Crossword puzzle clue "man should have money in his head but not in his heart swift"

"__ man should have money in his head, but not in his heart": Swift

Wondering "Should I? Should I not?"

"He's a complicated man/but no one understands him/but his woman"

Play a club when you should have played a heart

"Music should strike fire from the heart of man, and bring tears from the eyes of woman" speaker

Amazon tablet (Yeah, I probably should have included this as part of the theme, but I couldn't come up with a suitable answer.Sue me.)

Hasn't, but should have

It may have a head but not a tail