Dempster's darlings: Affairs with models, canoodling with Anna Wintour and his marriages to two heiresses

By Tim Willis
Updated: 04:39 EST, 4 October 2010

For 32 years, the Mail's diarist Nigel Dempster was Fleet Street's undisputed king of gossip. On Saturday, in our first extract from an uproarious new book about his life, we described how he used his sheer force of character to become the confidant of debs and dukes. Today, we reveal his fascination with aristocratic women  -  and his very complicated love life...

Handsome, debonair, witty and influential, Nigel Dempster never had any problems attracting women, particularly well-bred and well-off ones, for whom he had a particular penchant.

This led to unkind interpretations of his motives  -  which he did not help by labelling himself the ' founder president of Fortune Hunters Inc'. 

But he never let himself be kept, or distracted from his vocation as a gossip columnist dishing the dirt on the foibles of the rich, titled and famous. It seems he was just attracted to that sort of girl  -  and one can only applaud his taste.

The first was Carolyne Christie, niece of the Marquess of Zetland, whose family home was Jervaulx Abbey in Yorkshire.

They dated in 1964 and she thought him very glamorous  -  'much more sophisticated than the other boys on the debutante scene of cocktail parties and balls'. 

She loved his 'photographic memory and the anecdotes he embellished', while he was amused by the aristocratic nonchalance of her family. When he brought her home at breakfast time, her father, a racehorse trainer, clung on to his newspaper and told him: 'You can have my daughter, but not my Sporting Life.' 

But Carolyne never thought of their romance as being 'serious', and they went their separate ways.

His next love, on the other hand, was serious enough for him to propose marriage.

She was Audrey Hoare, of the banking family, whom he met after seeing her photograph in a newspaper in 1966. He rang and asked about her interests, which included the Mamas and Papas singing group. Soon after, she found California Dreamin' and Monday Monday posted through her letter box.

'He was so sophisticated,' she says, 'and amusing.'  But dangerous, too. 'I never told my parents that he was a gossip columnist and I was always very careful what I said in front of him.' 

So careful, indeed, that, rather than split up with him after rejecting his offer of marriage, she went round the world, leaving their three-year relationship in the air.

'I was scared he might write something about me.' 

On her return, she says, they both realised that ' the chemistry had gone', though not the friendship. Indeed, apart from a hiatus in the Eighties, when Dempster betrayed a confidence in print, his relationship with Audrey lasted his lifetime. 

The same went for his closeness with Anna Wintour, whom he escorted through the foothills of the glossy realm that she would one day make her own as the formidable editor of American Vogue.

A myth has grown up that Dempster 'went out' with the 16-year-old Wintour when he was 25. Again, he did not help by telling a story in which her disapproving father, Charles Wintour  -  then editor of the Evening Standard in London -  kept a beady eye on them. 

In this yarn, Dempster was dallying with her on the drawing room sofa at her home when he glanced over at the curtains, from under which he could see her father's suede shoes protruding.

Anna Wintour is adamant that this story is untrue. 'I don't think Nigel ever came to the house,' she says. 

She calls Dempster 'sweet', 'loyal' and 'a very good friend' who used to 'squire me around for openings and seemed pleased for the company'. But that was all. 'I can't make this more clear  -  there was nothing romantic about our relationship. I think he was just trying to take care of me.'

In his late 20s, Dempster decided it was time to find a wife. And though his choice was rich and aristocratically connected, she was not an obvious candidate, not least because she had a child in tow.

Emma de Bendern, sexy granddaughter of the Marquess of Queensberry, was said to have the 'naughtiest' face in London and the behaviour to match it. Bequeathed a fortune by her mother's first husband, she also inherited a wayward streak, and at 17 took up with a motorcycling petty criminal called Brian, giving birth to an illegitimate daughter.

Aged 21 and a single mother, she met Dempster in 1970 at the wedding of a friend.

'When he mentioned a horse he fancied for the next day  -  it was L'Escargot at Cheltenham  -  I wanted to show off so I gave him £20, which was a lot in those days, and asked him to put it on for me,' she says.

L'Escargot romped home and Emma rang Dempster to ask for her winnings. 'You'll have to come out for dinner to collect them,' he said.

After a breakneck romance, they had a grand wedding with a reception at Les Ambassadeurs. Bizarrely, Emma's mother joined the couple in bed for the first night of their marriage and they all cuddled up together.

The marriage fell apart in less than a year.

'The whole thing was a serious mistake,' said Emma. 'I did it for all the wrong reasons  -  for standing and security  -  but also for fun. I'd missed out on all that from having a child so young, and so it was very exciting to be taken to Ascot and to balls, and to meet all these lords and ladies.'

Dempster, too, must have thought he'd got a bit of a trophy  -  as Emma says: 'I was a countess, you know.'

But he'd bitten off more than he could chew. Marriage did little to curb the new Mrs Dempster's enthusiasm for unorthodox liaisons.

Six months after the nuptials, she was in the south of France, playing hooky with an antiques dealer named John Hobbs. Halfway through their holiday, Hobbs was rumbled by his wife and rushed home without packing.

Emma agreed to bring back his things  -  but when she arrived at Heathrow, she was told the case containing his clothes had been lost in transit. She arranged that, when found, it should be delivered to her neighbour.

This plan went disastrously awry when overzealous airline staff spotted the label reading 'Mrs Nigel Dempster'. Thinking they were obliging the rising media star, they dispatched it to him in Fleet Street.

'Poor Nigel,' chortles Emma, 'opened it in front of everyone, only to discover it was packed with another man's clothes.'

There were apparently fisticuffs between Nigel and Hobbs, but the divorce from Emma was painless.

In 1977, Dempster announced his engagement to an heiress and the daughter of a duke. Knowing looks were exchanged among his friends.

Lady Camilla Osborne's father was the bibulous and much-married 11th Duke of Leeds who  -  as Dempster never tired of repeating  -  was the brother-in-law of the Queen Mother. A tax exile with homes in Jersey and the South of France, he died when his daughter was 12. She grew up an only and lonely child who never quite blended into society. 

Though utterly blue-blooded, she was known as 'Commie Camilla', read the Guardian and agreed with its editorials. But her trust fund allowance and the £1 million she would inherit at 21 meant she attracted the attention of many journalists and suitors.

She married an advertising man but they divorced in 1973, leaving Camilla with a ten-month old daughter, Emily. Then, in 1975, it was announced - in Dempster's column, no less  -  that she was 'planning wedding number two' to a PR executive.

Unfortunately for the diarist's reputation  -  though not his future happiness  -  Camilla got cold feet, leaving her available when the pair met through one of her old school friends. 

He might not have seemed the dream husband for a very private person. 'Enough people told me he was trouble,' she recalls.

But something about him captivated her. Erika, his sister, remembers: 'Nigel didn't do the asking. It was Camilla who was determined to have him.' Camilla recalls him saying he was rescuing her from a dull life. 'I think he saw me as a challenge.'

They married at Chelsea Register Office in July 1977. No family from either side was invited. Two years later, their daughter Louise was born.

The marriage was much happier at the beginning than the end. They had in common a passion for the ballet, though his claim that he had a box at Covent Garden turned out to be a lie. She didn't mind. 'He said things just because he liked the sound of them,' she comments.

Most importantly, he made her laugh. When she was pregnant, they went to a drinks party where Princess Margaret was a guest. Finding the lift out of order, he dragged Camilla up several flights of stairs  -  and when the squiffy Princess began to commiserate with his expectant wife, cut in with: 'But that's social climbing, ma'am.'

Meanwhile, his marriage did nothing to dampen his enthusiasm for breaking sensational stories, and over the next three decades they were to make him, as he loved to boast, ' the greatest gossip in the world'.

One of his biggest scoops was the 1991 front page exclusive headlined 'Charles and Diana: Cause for Concern', as he revealed that Diana had refused all attempts by Charles to give her a 30th birthday party.

It was followed a year later by another that commanded the world's front pages: his revelation that Princess Diana had been suffering from bulimia for the first eight years of her marriage to Prince Charles.

Such stories depended on his attending countless social functions. Camilla would accompany him 'when they sounded like fun to me' (which they seldom did), but steered clear of his 'boy's club' of journalists and upper-class contacts. To her, his intimates seemed very immature  -  and 'no doubt they saw me as a killjoy and a nag'. 

Possibly, she was an obstruction, too. Some friends - notably the playboy and fellow writer Taki Theodoracopulos - are adamant that he chased other women. A colleague was aware of at least 'two half-hearted affairs' during his marriage to Camilla, and the writer Tessa Dahl claims that she had an enjoyable affair with him.

'I thought he was a great lover,' she says, 'though I know other women who say he wasn't so good in bed. But Nigel wasn't driven by sex so much as by people.'

They first met over the gaming tables at the Curzon Club  -  where the 15-year-old Dahl had been smuggled in by her father Roald.

She recalls that a friend of her father's 'told me Nigel had been paid off by some girl's father to stay away from her  -  so naturally I was fascinated'. 

Seeing him at a premiere three years later, she reintroduced herself, and soon became both his regular escort and a character in his column. 'I was unknown before Nigel started writing about me,' says Tessa. 'Then he contributed text about me to Patrick Lichfield's book on the most beautiful women in the world.

'I was very flattered, and we became mates - not dates; we didn't start with sex - and went to parties together.' She 'adored him', she says, 'and he seldom let me down. We both came from mongrel backgrounds and had the same view of people, the same jaded eye.' 

Dahl was married from 1981 to 1986 and again in 1991. Before and between those times, if with decreasing frequency, she would sleep with him  -  'at his house when his wife was away'  -  and though she was supposed to be a good friend of Camilla's, 'that was only by accident, because of my relationship with Nigel, so I never felt guilty about it'.

Citing all Dempster's usual attractions  -  his charm, kindness and humour  -  she adds to them 'his complications, and I like a complicated man'. To her, he seemed 'almost manic depressive'. One minute, 'he'd be proclaiming world domination', the next 'saying he'd screwed up his career'. 

But, she says, he had no delusions about himself: 'He knew he was a snob, he knew he could be impossible. He knew he wanted to be on an equal footing with his friends but wasn't really on the inside  -  and he knew he didn't really respect them. Those contradictions were the undercurrent of his life.' 

She remembers going with Dempster to a high society dinner 'when that crowd were at the height of their aristocratic arrogance', and suffering an evening of schoolboy sexual humour: 'Nigel joined in, but when we got back to the car, we just sat in amazement. He thought they were a bunch of prats.' 

Dahl is unwilling to take sides on his marriage to Camilla. 'People thought Nigel married her for the security and status,' she says, 'but he did love her, too, even if he was a bit frightened of her.'

She remembers him being 'absolutely devastated' when he discovered Camilla was seeing someone else. 'Still, he could be very naughty, and not the most loyal in his telling tales about the women both in and out of his life.' 

As for Camilla, she says she has no knowledge of her husband's infidelity ('And if I had found out, I'm sure he would have been able to convince me otherwise'). She thinks Dahl's stories should be taken with a pinch of salt. 

Their marriage did end, in 2003, after a quarter of a century together, but the breaking point was not any sexual shenanigans but Dempster's drinking. Increasingly he seemed determined to prove that he could perform better drunk than his rivals could sober.

He always broke up the day with a bottle of chilled Chablis  -  sometimes two, followed by champagne at El Vino's in Fleet Street. In his office, he kept an oxygen tank and mask behind his desk, so that he could take a blast and clear his head.

But Camilla had grown tired of it all. She decided she'd had enough and told him she wanted a divorce. Nevertheless, as we will see tomorrow, she was there for him in his declining years, when a terrible illness overtook and silenced the one-time king of gossip.

Extracted from Nigel Dempster And The Death Of Discretion by Tim Willis, published by Short Books on Thursday at £16.99. Tim Willis 2010. To order a copy at £15.30 (p&p free), call 0845 155 0720.