How to chat up an A-list woman: The surprising tricks that worked on a string of supermodels

So I’m having lunch with a friend and the supermodel Rosie Huntington-Whiteley when the subject turns to chat-up lines.
We both want to know what sort of one-liner has worked on the woman described as the most beautiful in Britain.
Needless to say, the cover star of magazines such as Vogue, who is currently dating the action star Jason Statham, claims to have heard them all — and insisted none of them had any effect. 

Fame wall: How do you chat up a star like Emma Watson, who complained at the weekend that men rarely pursue her?

Only once did Rosie nearly fall for a stranger’s seduction tactics.
A handsome man she encountered in a Los Angeles café seemed too busy with his own thoughts to be interested in flirting. She tried hair flicking and staring, but he wasn’t playing.
Then just as Rosie was about to leave, he caught her eye and raised a finger to his upper lip. ‘He had this moustache tattooed on his finger and he waggled it at me,’ she explained. ‘And that worked?’ I asked incredulously. Rosie smiled in confirmation.
Amazing, isn’t it? We men spend our whole lives trying to be urbane and amusing around women — but sometimes a waggle of a finger moustache is all a chap has to do to get a famous lingerie model’s attention.

Man about town: Simon Mills, pictured with wife Yasmin, is well versed in the ways of winning over famous women

Determined not be outdone, I borrowed a pen from a waiter and scrawled a Hercule Poirot upper-lip tonsure on my forefinger.
Then, when there was a break in the conversation, I waggled my finger at Rosie. It didn’t work as well this time (inexplicably, she seems to prefer millionaire movie stars to middle-aged men with grown-up children), but the gag put her at ease.
And by talking about chat-up lines, my friend and I established ourselves as being non-predatory. The ‘fame wall’ that surrounds celebrities had been broken by us keeping things breezy.

 At the weekend, actress  complained that men rarely pursue her. ‘It must be the fame wall,’ she said. ‘Me, as a person, I find it hard to believe I would be intimidating.’
Her advice to would-be suitors? ‘Be brave.’ 
Now, I’m not suggesting Emma is in my romantic crosshairs, but I know what she means about being brave.
Into my third decade as a showbiz journalist and party reptile, I’ve learned that a bit of risk‑taking is the important factor when trying to win over a fragrant celebrity.

Be brave: Diane Kruger, left, was initially frosty but thawed out, while actress Rosie Huntingdon-Whiteley, right, found a moustachioed finger an ice-breaker

Even the most beautiful women in the world want to have a laugh sometimes. If you want to approach a supermodel, you have to have the right brand of bravery. Cheeky-brave maybe, but not downright rude.
Like the time my outspoken friend Nick greeted a well-known TV celebrity at a book launch by saying: ‘What are you doing here? I didn’t know you could read!’ He got a glass of room-temperature Chardonnay thrown in his face.
You see, we ‘civilians’ tend to behave strangely around the famous. And the more famous and beautiful they are, the more peculiar our behaviour.

'My advice to young men in search of celebrity romance with the  of this world? Simply ignore them — at first'

At a cocktail bar, I once saw a man trying to win over actress Patsy Kensit by telling her she had fat ankles. She slapped him hard.
While talking to the singer Sharleen Spiteri at a party, another man — confident that he had equipped himself with a Wildean quip — barrelled up and said: ‘Your last album was rubbish, wasn’t it?’ 
She took him to task. ‘And how did you think that comment was going to endear me to you? Did you think we would become great friends after that?’
The man sloped off looking crestfallen. But although an insult never works, it’s important to go easy on the compliments, too. Models and actresses are constantly told that they are beautiful, so don’t bother trying that.
I was introduced to Cindy Crawford recently, and we talked about the joys of the iPad backgammon application. I even persuaded her to try her hand at Scrabble. I didn’t come on like a simpering fan, nor was I too familiar.
My advice to young men in search of celebrity romance with the Emma Watsons of this world? Simply ignore them — at first.
If you want to win over these beauties, talk to her non-famous friends instead.
Not being at the centre of things is torture for beautiful girls and they will soon want to find out why you don’t appear to be interested in them.
Flying to New York on Concorde with 20 or so Victoria’s Secret lingerie models for a magazine shoot a few years ago, I decided to sit on my own at the back of the plane.

Getting Danni Minogue's attention was as simple as buying a caramel Kit-Kat

Mainly because I was one of only a few men on the flight, the girls soon became curious as the champagne flowed.
One by one, pretty much every Bambi-legged beauty came and sat next to me for a friendly chat.  
Ignorance is often productive, too. At a wedding in Istanbul, I sat next to the actress Diane Kruger, who had recently played Helen of Troy in a Hollywood blockbuster.
She was frosty at first, but when it became evident that I genuinely had no idea who she was, she thawed out.
When she said she was an actress, I asked: ‘So, been in anything I’d know?’ ‘I’m in a film called Troy with Brad Pitt,’ she replied, a bit defensively. I blushed. Diane laughed it off with grace. We got on just fine after that.
Doing a bit of research can also pay dividends. Before meeting Dannii Minogue, I found out that she was partial to caramel Kit-Kats, and casually pulled one from my pocket while we were talking. ‘How did you know?’ asked the cute Aussie star as she took a bite. I didn’t tell her, but getting Dannii on my side had cost just 45p.
In conversation, always presume even the most air-headed beauty is blessed with fine taste and an opinion.

'If you see a beauty, chaps, don’t be afraid to approach her - but for goodness’ sake follow my advice if you don’t want to go home covered in Chardonnay'

Ask what she thinks about a new exhibition or novel. I’ve found it’s best to stay off the subject of work, although if it’s unavoidable, always compliment your famous friend on their latest side project. Especially if its something niche and tangential. 
If you encounter a model, don’t bang on about her latest campaign for Calvin Klein, but inquire how the photography is going.
I once spent a very pleasant ten minutes discussing ayurvedic treatments with Christy Turlington.
I had no idea what I was talking about, but I managed to convince the world’s second most beautiful woman (after Mrs Mills, of course) that I did. You see, being zeitgeisty is everything in showbusiness.
Does all this sound a bit exhausting? That’s because it is. Make no mistake, the civilian/celebrity liaison can be thrilling — but it can also be precarious.
When you fall out, things can get ugly. One friendship I had with a well-known actress ended with a three-page fax of invective and a letter from her lawyer after I made unflattering comments about her, while a female TV presenter I’d got to know well once threw a drink over me at a nightclub. Although we got on much better after that.
So the message is: if you see a beauty, chaps, don’t be afraid to approach her — but for goodness’ sake follow my advice if you don’t want to go home covered in Chardonnay.