Born in Sanquhar Castle, his home was at Fingland only 12 miles from Annie's Maxwelton, but they appear to have had their first meeting at an Edinburgh ball. They fell in love, but there were complications. Annie's father, who had been knighted by James VII two years after she was born, was a strong Royalist and a vigorous persecutor of Jacobites and Covenanters--not surprising since he was a cousin of the notorious butcher of Covenanters, Grierson of Lag. Indeed, it was in recognition of his anti-Jacobite and anti-Covenanter activities that he received his knighthood.

Captain Douglas, on the other hand, was pledged to the Stuart cause, a Jacobite to the backbone, so that Sir Robert's attitude towards him as a son-in-law was less than enthusiastic. In any case, Douglas was something of a rough diamond, an expert swordsman with a fiery temper that landed him in a succession of duels. Legend has it that on one occasion he was literally crossing swords with Sir Robert when Annie came on the scene and put an end to it. Another opponent, wounded and disarmed by Douglas, later declared that he was defeated less by Douglas's skill than by his "fierce and squintin eyen".

Despite Sir Robert's disapproval, Annie and her lover continued to meet secretly in the seclusion of Maxwelton Braes until news came that a Stuart invasion was about to be launched. Captain Douglas had to leave at once for Edinburgh, but before he spurred away he penned his poetic tribute to his loved one, making up in passionate enthusiasm whatever may have been lacking in elegance and literary merit. Here is how he described the, apparently, shapely Annie:

She's backit like a Peacock,

She's breastit like a swan,

She's jimp about the middle,

Her waist ye weill may span,

Her waist ye weill may span,

And she has a rollin' eye,

And for bonnie Annie Laurie

I'll lay down my head and die.

Like his grandfather, James of Morton, he was a Commissioner of Supply in Dumfries, in 1693