[1] He was the son of Robert Ainslie and his wife Magdeline Elliot of Woolie, described by Burns as "an excellent, sensible, cheerful, amicable old woman"; he was born at Berrywell House near Duns in 1766.

Writing in pencil on the blank leaf of her bible[7] that "Fair maid, you need not take the hint, nor idle text pursue: 'twas guilty sinners that he meant, not angels such as you.

"[4] He hoped to set her mind at ease after the minister's sermon on the terrors of hellfire for the sinner and her searching her bible for the text.

[1] Ainslie's own office as a Writer to the Signet was in the Edinburgh New Town at Hill Street; and he also had a country estate at Edingham in the Stewartry of Kirkcudbright.

[2] Robert Heron said of Ainslie that he was "[...] a gentleman of the purest and most correct manners, who was accustomed sometimes to soothe the toils of a laborious profession, by an occasional converse with polite literature, and with general science.

[2][13] As a student Ainslie lived at No.6, St James's Square in Edinburgh and his near neighbours were George Thomson the music publisher, the artist John Beugo, the engraver and Alexander Nasmyth the painter, all of whom were more or less closely associated with Burns's career.

[15] Ainslie, having been granted two weeks leave, accompanied Burns on his travels and the pair left Edinburgh on 5 May 1787 beginning the first stage of the Borders Tour.

At Eyemouth they both were inducted as Royal Arch Masons at St Abb's Lodge: Ainslie had to pay a fee but Burns was excused on account of his poetic genius.

Ainslie crossed first, followed by Burns who fell to his knees and is said to have quoted the last two patriotic verses of "The Cotter's Saturday Night" - "O Scotia!

Then, howe'er crowns and coronets be rent, A virtuous populace may rise the while, And stand a wall of fire around their much-lov'd Isle."

"[8] He also commented in his sporadic Border's Journal on Ainslie's sister Rachel, saying that "My bardship's heart got a brush from Miss Betsey'; I could grasp her with a rapture on a bed of straw, and rise with contentment to the most sweltering drudgery of stiffening labour.

He commented also that "One day he sits down and writes a beautiful poem - and the next seize a cargo of tobacco from some unfortunate smuggler, or roups out some poor wretch for selling liquors without a licence.

The proud heart of Burns did not like this humbling, after a few wrathful words in secret to one of his friends, he took a pencil and wrote these lines on the envelope.

"[30] "In politics if thou would'st mix, And mean thy fortunes be; Bear this in mind, be deaf and blind, Let Great folks hear and see.

"[30] Ainslie is said to have confirmed that Burns had been a covert member of the Society of the Friends of the People which strove for parliamentary reform until suppressed by the government.

[31] It was Ainslie who visited Alexander Cunningham as a lawyer on behalf of Agnes Maclehose to demand the return of the letters that she had written to Burns.

"[2] The sentiments "You assume a proper length of face in my bitter hours of blue-devilism (depression), and you laugh fully up to my highest wishes at my good things.

It seems that from a letter to Ainslie on 2 March 1788 that Burns had negotiated a reconciliation between Jean Armour and her mother so that she would be able to attend her daughter during her confinement.

The original letter may be the one that the antiquarian book-seller James Stillie and a group of friends purchased for £4 and put into the fire in an attempt to protect the bards reputation.

I am truly pleased with this last affair: it has indeed added to my anxieties for Futurity but it has given a stability to my mind & resolutions, unknown before; and the poor girl has the most sacred enthusiasm of me, and has not a wish but to gratify my every idea of her deportment.!!!

— Ask her for a letter I wrote her just now, by way of token " Burns added the telling instruction, "but don't for Heaven's sake meddle with her as a Piece.

[39][40][4] On 23 June 1788 Robert informed Ainslie that he had arranged a sitting with John Miers to produce a profile or silhouette picture and that together with one of Lord Glencairn and Dr Blacklock he intended to hang them on his new mantlepiece at Ellisland Farm.

[42] On 30 June 1788 Robert Ainslie wrote and informed Burns that now Agnes Maclehose's servant girl, Jenny Clow was pregnant by him.

[43] On 6 January 1789 Burns wrote to Ainslie to say that he hoped to be Edinburgh in February to meet Jenny and to "settle the matter with her, and free her hand of the process."

[44] In 1789 Burns wrote of his attitude towards his job with the Excise, saying "I have the same consolation which I once heard a recruiting sergeant gave to his audience in the streets of Kilmarnock: 'Gentlemen for your further encouragement, I can assure you that ours is the most blackguard corps under the crown, and, consequently, with us an honest fellow has the surest chance of preferment.'

"[45] Circa May 1792 Burns wrote to Ainslie at a very low ebb ".. My wife scolds me, my business torments me, and my sins come staring me in the face, every one telling a more bitter tale than his fellow.

[46] On 26 April 1793 Burns wrote again in a depressed mood and included a witty story of a subscriber to the reading library he was involved in to whom he "advised him, instead of turning over the leaves, to bind the book on his back."