My entree into online chat was the AOL chat rooms - on dial up. As the years moved forward, still on dial-up, Yahoo soon supplanted AOL as my chat source of choice. Back then there were so many amazing rooms and often regional or local rooms. Yahoo also allowed for user-created rooms and that helped really target the chat.
I will admit that those chats at times led to offline relationships that were extramarital in nature. More often taking the oline experience to phone, but sometimes there were flings and even full blown affairs as a result.
