Earlier quoted context omitted.
Perhaps there's a difference if you meet someone who is already successful or who's past accomplishments you admire versus that idiot in high school who barely passed chemistry by cheating off your answers, exibited the worst of the sexist jock/bro mentality, skated by on his good looks and is now driving a lambo and married to a supermodel.
I can't understand why someone over 25 that has a decent career (assuming you are a programmer since it's HN) would still care about what some chad from high school is doing. Worrying about how "unfair" life is is an energy and time black hole.
See also Dahl's "galloping Foxley" for a literary take on the phenomena.