I was also still using ICQ in addition to AIM in 99/00.

Quick story - you could search for ppl by name on ICQ so I searched up a girl I had a big crush on. I was about 17, so I found her and we started chatting one Friday night. I got the courage to ask her out after talking for a little bit and she replied "I have a boyfriend". In a rare act of ballsiness I replied "so break up with him". She immediately replied "brb" to which I thought she was going to the bathroom or her Mom called her downstairs or something. About two minutes goes by and she came back and said "okay I did it". Chatted all weekend and started dating officially as bf/gf that Monday at school.

Good times.