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The recent increase in attention being paid to the experience of loneliness (Booth, 2000; Franklin & Tranter, 2008; Hawkley & Cacioppo, 2010; Ord, 2018; Smyth & Goddard, 2018), and a serendipitous alighting on a trove of old journals and letters from my past, has given me a chance to reflect on loneliness and what it means. The result is this reflective and semi-autobiographical essay that offers personal insights into the nature of loneliness. Some thoughts are offered with regard to the dilemma it creates for therapy.