Boswell returned to London in February
1766 accompanied by Rousseau's mistress, with whom he may have had a brief affair on the journey home. After spending a few weeks in the capital, he returned to Scotland to take his final law exam. He passed the exam and became an
advocate. He practiced for over a decade, during which time he spent no more than a month every year with Johnson. Nevertheless, he returned to London each year in order to mingle with Johnson and the rest of the London literary crowd, and to escape his mundane existence in Scotland. He found enjoyment in playing the intellectual rhyming game
crambo with his peers.
Boswell married his cousin, Margaret Montgomerie, in November
1769. She remained faithful to Boswell, despite his frequent liaisons with prostitutes, until her death of
tuberculosis in
1789. After his infidelities he would deliver tearful apologies to her and beg her forgiveness, before again promising her, and himself, that he would reform. James and Margaret had four sons and three daughters. Two sons died in infancy; the other two were
Alexander (1775-1822) and James (1778-1822). Their daughters were Veronica (1773-1795), Euphemia (1774-ca. 1834) and Elizabeth (1780-1814). Boswell also had at least two illegitimate children, Charles (1762-1764) and Sally (1767-1768?).
Despite his relative literary success with accounts of his European travels, Boswell was an unsuccessful advocate. By the late 1770s he descended further and further into alcoholism and gambling addiction. Throughout his life, from childhood until death, he was beset by severe swings of mood. His depressions frequently encouraged, and were exacerbated by, his various vices. His happier periods usually saw him relatively vice-free. His character mixed a superficial
Enlightenment sensibility for reason and taste with a genuine and somewhat
Romantic love of the sublime and a propensity for occasionally puerile whimsy. The latter, along with his tendency for drink and other vices, caused many contemporaries and later observers to regard him as being too lightweight to be an equal in the literary crowd that he wanted to be a part of. However, his humour and innocent good nature won him many lifelong friends.
Boswell was a frequent guest of Lord Monboddo at
Monboddo House, a setting where he gathered significant observations for his writings by association with Samuel Johnson,
Robert Burns, Lord Kames, Lord Monboddo and other luminaries.
After Johnson's death in
1784, Boswell moved to London to try his luck at the English
Bar, which proved even more unsuccessful than his career in Scotland. He also offered to stand for Parliament but failed to get the necessary support, and he spent the final years of his life writing his
Life of Johnson. During this time his health began to fail due to
venereal disease and his years of drinking. Boswell died in London in 1795.