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Journalistic confession, for Boswell, covered a range of activities and needs apart from his recurring depression, though some of these also had the tendency to feed that depression. This is particularly the case in respect of his frequent promiscuity, when his behaviour is recalled sometimes with relish, sometimes with regret, and often with a mixture of both. A sequence of events that took place in Edinburgh between November and December 1776 is illustrative. On Monday 25 November, Boswell, who should have been working at law-papers, instead argues with his wife, Margaret, and leaves the house. Later, ‘coming home at five,’ he writes, ‘I met a young slender slut with a red cloak in the street and went with her to Barefoots Parks and madly ventured coition. It was’, he adds, ‘a short and almost insensible gratification of lewdness. I was vexed to think of it.’ Vexed or not, two evenings later, in the High Street, he ‘met a plump hussy who called herself Peggy Grant’ and ‘went with her to a field behind the Register Office, and boldly lay with her. This was desperate risking.’ It was, Boswell interjects, ‘one of the coldest nights I ever remember’. Even more ‘desperate’ information is revealed in the following day’s entry:

The girl with whom I was last night had told me she lodged in Stevenlaw’s Close, and at my desire engaged to be at the head of it generally at eight in the evening, in case I should be coming past. I thought I could not be in more danger of disease by one more enjoyment the very next evening, so went tonight; but she was not there.

He finishes the day by observing: ‘I was shocked that the father of a family should go amongst strumpets; but there was rather an insensibility about me to virtue, I was so sensual. Perhaps I should not write all this’ - ‘all this’, from Monday through till Thursday, in fact being written on Friday 29 November. On Sunday 1 December, however, a crisis is reached. Boswell, listening to a sermon, is already sketching out his evening:

I must confess that I planned, even when sober, that I would in the evening try to find Peggy Grant, and, as I had risked with her, take a full enjoyment.... About eight I got into the street and made Cameron, the chairman, inquire for Peggy Grant.... He brought her out, and I took her to the New Town, and in a mason’s shed in St. Andrew’s Square lay with her twice.