Not 100% sure but to keep the game going I'll let someone else get it with my general guess hint

Henry to someone (maybe but I doubt Karen) before going to prison for the first time.

Hey there buddy, What’s Up? Patricia told us you were coming. My name is Luke and I’m team hoarden all the way. I ain’t no bad hombre. Everybody’s gonna tell you I got a big mouth though. I spoil the endings to movies. -Dennis from GLASS

Hey, can we keep it under 60? I’m still trying to pay for all this dental work. -Simon from TRUE LIES