Good times but also not so great times too...
I remember when i was very young and msn was very popular, my uncle was using it, and there was this bot that would talk to him, he was showing me it. It may have been smarterchild, who knows, i was young and had no idea.
He then started laughing so i went to his computer and asked why, and he said look. I looked at the screen and saw this other woman (had a female name) talking to my uncle casually but calling him penis. My uncle said that it wasnt a real person but a bot, and the bot thought his name was penis.
It went something like this
Uncle: Hi how are you?
Bot: Hi, penis, i am good, you?
Uncle: Thank you, yes i have been on holiday
Bot: Good on you penis, we should go together sometime.
Not exactly that, but generally what i remember was holiday and penis.
Thats probably the most vivid memory i have of MSN. For some reason, it still makes me laugh.