Who is your oldest friend (i.e., the friend you have known the longest)? How often do you see or talk to each other? Do your close friends tend to stay the same year after year or change over time?
Longest time overall, planning to get back with sometime? Katie from church back in the high-school years. Close to 30 years. Found again on Classmates.com and facebook. My philosophies have changed so much, though, and her core values seem to be pretty much the same, so I don't know how long the friendship will last after our next meeting!
Longest time and still actually see/visit/have lunch with? Donna who was a teacher/dean where I went to business school -- 'tema was in, I think, second grade? So 20 years there! Donna has watched my progress/treansition/growing-up and laughed at me all through it, but in a non-insulting way! Our philosophies are very different, but we agree to disagree and enjoy what we have in common.