Hello. I don't know what the underlined phrase below means.
"I used to weart that thing all the time."
"Good God, I hated that thing," Dad laughed, almost more to himself.
"I was so bummed when it got lost."
He was talking and laughing, but it wasn't important that anyone hear him. He was talking to himself as much as he was talking to whoever else was there.
I'm not a teacher, but I write for a living. Please don't ask me about 2nd conditionals, but I'm a safe bet for what reads well in (American) English.