I was prob high as shit and thought this was actually funny.
This was in my freshman year of college and I was into a girl who went to a different school than me (but only like 45 mins away, so it wasn't really that serious), so I considered that 'too long distance to work out'. The last unfunny entry in this list was inspired by that.
Other stuff was based in reality too. I was prob reflecting on times in high school when I'd get wasted and call people and end up saying emotional stuff. Or cringing at other embarrassing stuff I did in high school relationships. Other stuff I'm not sure where it came from - I never broke up with anyone on AIM.