Austen's very own Mr Darcy

Mr Darcy, the brooding landowner who, after a series of misunderstandings, seduces the spirited Elizabeth Bennet in Jane Austen's Pride and Prejudice, is one of fiction's favourite romantic heroes. This week, a rare miniature portrait of the man who some believe may have provided the inspiration for him is going on sale.

One of only two paintings known to exist of Thomas Langlois Lefroy, a 20-year-old law student who met Jane Austen while he was visiting his aunt and uncle in Hampshire, it shows an attractive and sensitive-looking young man dressed in a blue velvet jacket and white cravat. An original watercolour by George Engleheart, it was painted in 1798 and is going on sale for £50,000.

Austen was also 20 when she met the portrait's subject, and for a blissful few weeks the young pair delighted in one another's company, dancing and talking together whenever the occasion allowed. But their youthful flirtation was not to last. As the son of an impecunious family, Lefroy was expected to marry an heiress and as soon as his relations noticed the growing affection between him and Jane, he was whisked away from danger.

Last year, the film Becoming Jane, starring Anne Hathaway and James McAvoy, told the story of their relationship. Now, the sale of the miniature looks set to reignite speculation surrounding one of the only real love stories of the woman who brought so many romantic encounters to life in her novels.

The watercolour, which is painted on ivory and measures just 3 inches by 1 ¼ inches, is on display at the Grosvenor House Art and Antiques Fair, at Park Lane in London, from Thursday. It is by Engleheart, the great English miniaturist, and the only one which is dated and signed with the artist's distinctive cursive E. The other portrait remains in the hands of Lefroy's descendants.

Brian Harden, one half of the Gloucestershire-based specialist dealers Judy and Brian Harden, who are selling the painting, said: "We bought this at auction quite a long time ago and it's been in our private collection since that time. We didn't know whom Tom Lefroy was when we bought it – it went through the auction house unrecognised – but we were able to identify and discover the history of the sitter. It's a very fine piece. The sitter is very handsome and personable. It was painted just two years after he met Jane Austen."

He added: "George Engleheart was one of the major society painters. He was a meticulous recorder of his sitters."

Austen, who met Lefroy in 1796, referred to him in a letter as "a gentlemanlike, good-looking, pleasant young man". Later, she said he had "but one fault, which time will, I trust, entirely remove – it is that his morning coat is a great deal too light".

Whatever hopes Austen had of Lefroy, they were soon to be dashed. His family, who were of French Huguenot origin, were not wealthy, and were relying on him, as the eldest son of 10 children, to marry a woman of substantial means. Austen, a clergyman's daughter, did not fit the bill and he was promptly removed from the situation.

Shortly before they parted, Austen wrote: "At length the day is come on which I am to flirt my last with Tom Lefroy ... my tears flow as I write at the melancholy idea."

Three years later, Lefroy married Mary Paul, an heiress of whom his family approved, and he went on to enjoy a successful legal career, becoming chief justice of Ireland in 1852. In later life, Lefroy, who named his eldest daughter Jane, admitted that he had been in love with Austen, but described it as "a boyish love".

This early experience of romance, coupled with the ensuing sense of injustice, may have provided Austen with the inspiration for the love affair between Fitzwilliam Darcy and Elizabeth Bennet in Pride and Prejudice – although the novel, of course, has a much happier outcome. To add fuel to the speculation, d'Arcy was a well-known name in Anglo-Irish legal circles at the time.

However, the biographer Claire Tomalin, author of Jane Austen: A Life, believes that, while Tom Lefroy undoubtedly influenced the novelist's fiction, he was not the model for Mr Darcy. "The first letter that has survived of Jane Austen's is all about meeting Tom Lefroy. He was the nephew of close friends and neighbours of the Austen family. He came for a few days' holiday and he and Jane went to the same dances and really liked one another. What seems to have happened is alarm bells rang – Jane Austen had no money, he had no money – so he was sent smartly back to London.

"This is how writers work. I think that she was in love with him and I think that she felt humiliated by what happened. She then used this emotional knowledge when she could to write about similar things in her novels. All writers draw on their own experiences, but Darcy was a landowner and Tom Lefroy a penniless law student. There's no connection."

Professor Janet Todd of the University of Aberdeen believes that Lefroy was nothing more than a youthful flirtation for Austen. She said: "She obviously did flirt with him, and she obviously felt pained at losing him, but I feel certain that he's not the main love of her life. There's somebody a bit later who is clearly really important. She talks about it with a lightness that makes it unlikely she was smitten. The letters suggest a flirtation, but she's rather proud of the fact that she seemed to be a bit in love and lost. She sees herself as a fictional heroine."

Professor Todd agreed with Tomalin: "Mr Darcy is everybody's idea of the silent, passionate hero. I can't see there's anything in Tom Lefroy that seems like that. He seems more like Frank Churchill [a character in Emma, who flirts with the heroine, but is betrothed to someone else], very pleasant and talkative."

When literature imitated real lives

James Bond, hero of Ian Fleming's novels, inspired by Patrick Dalzel-Job

The 007 creator put a lot of himself into Bond, but other real-life characters have been cited as inspirations as well, among them Sub-Lieutenant Patrick Dalzel-Job.

The commando worked for Fleming as part of his wartime intelligence work in 30 Assault Unit and was described by Ben Macintyre, the author of a book accompanying the Imperial War Museum's recent Bond exhibition, as "an extraordinary man of quite lunatic bravery".

In 1940, at the age of 27, Dalzel-Job organised the rescue of 5,000 civilians using a fleet of 200 fishing boats from the town of Narvik in northern Norway as the Nazis approached. An accomplished skier, parachutist and diver, Dalzel-Job was then seconded to work for Fleming helping to sabotage the German war effort.

Despite the similarities, however, Fleming never confirmed that the young troop commander was one of the inspirations for Bond and in a recent interview with the Edinburgh Evening News, Dalzel-Job's son Iain said that, when pressed on the subject, his father said he had "only ever loved one woman" and was "not a drinking man".

Miriam Staynes, DH Lawrence's heroine in 'Sons and Lovers', inspired by Jessie Chambers

D H Lawrence first met Jessie Chambers, who is sometimes described as his first girlfriend, when he was 15 and the pair enjoyed an intense – if sexless – friendship. As they grew older, the writer's relatives tried to dissuade him from the relationship, which had begun to be talked about in a manner they weren't entirely happy with.

Ever devoted to the writer, Chambers put up with Lawrence's affection for a string of other women. At the age of 27, however, he finally broke her heart for good when he eloped to Germany with Frieda Weekley, the wife of a Nottingham University lecturer who had once taught him – she was also a distant relative of the "Red Baron", Manfred von Richthofen.

Lawrence eventually married Weekley, who left her three children behind to elope with him. Chambers is thought to have been the inspiration for Miriam Staynes, one of the main characters in Sons and Lovers. Paul Morel, a miner's son, derives "the most intense pleasure" from discussing his work with Miriam, mirroring the youthful conversations between the real-life friends. In his younger days, Lawrence would often walk from his home to visit Jessie, who lived on the nearby Haggs Farm.

Little Nell, Charles Dickens' tragic heroine in 'The Old Curiosity Shop', inspired by his sister-in-law, Mary Hogarth

Dickens was much affected when his sister-in-law Mary, of whom he was extremely fond, suddenly fell ill and died in his arms while he and his family were living at 48 Doughty Street – a row of Georgian terraces near Bloomsbury. Hogarth, the sister of Dickens' wife Catherine, was 17 when she died in 1837.

The death left such an impression on the writer that, a few years later, he recalled it in the death of his beloved heroine Little Nell. Fleeing with her grandfather from the evil money-lender Daniel Quilp, Nelly Trent is exhausted by hunger and meets a premature end while wandering in the bleak Shropshire countryside.

In his instructions to the illustrator George Cattermole for the deathbed scene, Dickens wrote: "I want it to express the most beautiful repose and tranquillity and to have something of a happy look, if death can ... I am breaking my heart over this story, and cannot bear to finish it."

Meyer Wolfsheim, mobster in F Scott Fitzgerald's 'The Great Gatsby' inspired by Arnold Rothstein

The son of respectable members of New York's Orthodox Jewish community, and the brother of a rabbi, Arnold Rothstein turned prohibition to his advantage and became a racketeer. Fitzgerald caricatured him as Jay Gatsby's friend Meyer Wolfsheim – "the man who fixed the World's [sic] Series".

He was suspected of setting up the defeat of the Chicago White Sox, although he was later cleared. In his biography of Rothstein, Nick Tosches said Meyer was a gross caricature. Fitzgerald said he had met him and drawn on that experience.

Orlando, Virginia Woolf's aristocratic man-woman, inspired by Vita Sackville-West

'Orlando' tells the story of a young aristocratic man born in the reign of Queen Elizabeth I who decides he is not going to grow old. It follows him through several ages of history, until he wakes up one morning to find he is a woman.

The book was described by Woolf as a biography, as she intended it to be a semi-fictional account of her friend and lover Vita Sackville-West, who was born into a wealthy, upper-class family but was barred by her sex from inheriting the family seat, Knole House in Kent.

A love affair between Orlando and the exotic Princess Sasha is a thinly veiled account of the romance between Sackville-West and the novelist Violet Trefusis. Woolf, who enjoyed a passionate affair with Sackville-West herself, got away with the risqué story because Orlando is a man at the point at which he falls in love with the princess.

Nigel Nicolson, Sackville-West's son, said Orlando was "the longest and most charming love letter in history".

William Boot, Evelyn Waugh's reporter, inspired by Bill Deedes

The "Grand Old Man of Fleet Street", who died last year aged 94 following a prolific journalistic career, was supposedly the inspiration behind the green young war reporter in Evelyn Waugh's celebrated 1938 novel.

In a hilarious chain of events, Boot, who writes a gentle column on country life for a London newspaper, the Daily Beast, is mistakenly sent as a foreign correspondent to the fictional African country of Ishmaelia.

It is a far cry from his usual beat, which requires him only to write such overblown prose as: "Feather-footed through the plashy fen passes the questing vole." Waugh was widely assumed to have based his hapless character on Deedes who, as a junior reporter on the Morning Post, was dispatched to cover the war in Abyssinia.

Deedes later wrote: "I am no more William Boot than I am the Man in the Moon", but conceded that Waugh, a fellow journalist at the time, had been much amused by his arrival in Addis Ababa with a quarter of a ton of luggage. The author included this detail in his portrait of Boot, who turns up to cover the war in Ishmaelia with a similar amount of supplies – including cleft sticks, an "overfurnished tent" and "a portable humidor".