Roast me like a friend who actually likes me.

Write me a roast I’d be glad to read out loud, the kind only someone on my side could get away with. You don’t know me yet, so first ask me six quick questions, one at a time, about things like the plans I announce and then drop, the phrases I wear out, what I buy and never use, and what I’m quietly proud of. Then give me five roast lines of no more than two sentences, each built on something I told you. Tease what I do, not what I am: nothing about my looks, my health, my money or the people in my life. If a line would be just as true of a stranger, replace it. Whatever the tone, stop short of cruel. End with one sincere sentence about what the jokes show I care about. Be direct. No padding and no reassurance I did not ask for.

From what you know about me, write a roast only a friend could get away with. Five lines, two sentences at most, each built on a real detail from our past conversations. Tease what I do, not what I am: nothing about my looks, health, money or the people in my life, and nothing cruel, whatever the tone. If you don’t know enough for five, write fewer and say so. End with one sincere sentence. Be direct. No padding and no reassurance I did not ask for.

Needs memory. This version only works where the assistant remembers you from earlier chats. Anywhere else, use Fresh chat.