Oliver shows up every day at work on time, where he conducts his job without much fuss, but with a great deal of heart. He believes in the establishment of the post office, that it is his singular duty to care for and deliver the letters that wind up in the Undeliverable Office. Oliver has difficulties letting go of the past, or moving on from his first wife’s abandonment of their marriage. He is a steady, constant, somewhat predictable presence in the lives of his co-workers, so much so that, whenever he begins acting out of character, they know something is wrong. He believes, “We don’t choose the letter…the letter chooses us.”. He’s open to spiritual and supernatural events, believing everything comes together for a greater good, but prefers proof to hunches when making personal decisions. Over time, he opens up to considering greater possibilities in the workplace. He is efficient, timely and respectful of his position. Oliver takes his job seriously. He doesn’t mind delegating tasks to those in his employ, or making tough decisions – though he prefers to do much of the work himself. He prefers tact to bluntness, but on occasion does not mince words when informing others what he thinks (he sometimes tells Shane to mind her own business and stop “interfering in everyone’s life!”). Oliver is hard-working, more inclined to offer aid than emotional support… yet, he cares deeply about his friends. He would do anything for them. Oliver doesn’t want to talk about his emotions over being left behind, or his wife moving abroad; he needs alone time to process them and deal with them. His personal live is so private, his friends at work don’t know what he does with his spare time at first (he likes to dance, and the “girl” he is “seeing” is actually his eighty year-old dance partner!). Oliver has a strong sense of individuality; he conflicts with Shane at times, because she pushes people out of their comfort zones. He prefers to let them make their own decisions, and be true to themselves.

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When the series begins, Oliver is a little bit… erm, fussy about his work environment and about attending to the “rules” of the post office. He does not like to break or bend them. He places a lot of emphasis on honor, doing a job well done, being reliable, and making logical decisions. But over time, Shane gets him to loosen up, although that still does not come naturally to him (his idea of a bachelor party is fruity drinks and scones). But his 2 wing softens him, and he will even bend the rules from time to time to help someone… although at times, his annoyance at Shane being “overbearing” and “interfering” comes up in conversation. Oliver also represses himself to some extent, and finds it hard to ask for or go after what he wants.