Quote:
...
<nick1> I'm tired. I only got a measly 3 hours sleep last night.
<nick2> I an XX year old male/female and live in XX.
<nick1> OK... So anyway, I think I'm about to fall asleep
<nick2> I an XX year old male/female and live in XX.
...


Regular expressions to the rescue!:
Code:
on $*:text:/\ba([\.\\\/-]?)s\1l\b/Si:?:{
  msg $nick I'm XX years old, male/female, and live in XX.
}