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I was friends with one of my exes for several years after we broke up. However, eventually I came to realize that that despite reaching his mid twenties he was still trapped in his stunted adolescence and patterns of self destructive behavior that made me dump him in the first place. It just hurt to much to watch him waste all the intelligence and talent as a writer that I knew he possessed while he waits tables for a living, gets drunk every night, and has actually managed to increase his drug use. After a while you just have to walk away.
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