A phrase that is difficult to say well is “I really care”, try saying it at a funeral, or when someone tells you their kid just died, I really care.
My father told me of an incident that happened to him when he was a kid, back in the 1930s. He was standing in line at movie theater, ready to pay his nickel for a ticket. The teenage girl who was in the booth was talking to a friend of hers through the open door of the booth. He tried to interrupt her, to get his ticket.
He said she turned toward him, looked at him, and said “die, kid.”
Just to show, it was going on 90 years ago.
That's a risky thing to say with sincerity. What if the response is, "Really? 'Cause I desperately need $5,000 to cover the funeral expenses! Thanks for offering!"
Regards,