David, one of our long-time community members and frequent finder of thought-provoking articles for this blog, sent me this story recently.

I think it’s quite interesting, and I’d love to hear some experiences you’ve had with this issue. That is: how do you handle developing and maintaining friendships with people who have a very different income/net worth than you?

Personally, I’ve found my best experiences regarding this to be had by adhering to the following rules: I remain close to friends I’ve known since adolescence. There’s little room for pretense, and the bond created during the school years endures for some delightful and mysterious reason, income inequality be damned.

Second, I keep my radar up for any favors or requests being asked of me at the start of a relationship. And by ‘start’ I mean the first 2 years. I notice whether or not a new acquaintance picks up the check for coffee every other time we meet, or if I’m always the one paying. If I have to read between the lines of a conversation, that’s telling. I listen for names being dropped. I watch for the presence or lack of gratitude.

Third, I never ask any affluent or famous person for anything. They’ve seen and heard it all, and they can sense the disingenuous. They can also see a request for a favor or money coming a mile away. If they are cynical or of a suspicious nature, their suspicions will go unfounded with me. If they are of a generous nature, after a period of time without being solicited, they will inquire about my aspirations and interests and ask if there’s something they can do to help. Only then will I speak in general terms about any projects I’m working on or any goals I have.

As I said, I’d love to hear your experiences, and any guidelines that you follow.

Martha Alexander’s insightful piece appears below, reprinted from Tatler. Enjoy, and thank you very much, David.

Can friendship ever bridge a wealth divide?

‘While on a global scale, I’m affluent and privileged beyond belief, in the microcosm of an English public school, I was more orphan Annie than Daddy Warbucks’

My first car was a Nissan Sunny. It was bruise blue and looked like it had been fashioned out of paper, a boxy toy that looked as if it might blow away on windy days.

I was, of course, lucky to have a car, any car, even one which required me to lift the bonnet and smack the starter motor with a stick whenever I wanted to move it.

What was unlucky for me, was that the sixth form car park of my girls’ boarding school, Queen Margaret’s in York, was something of a showroom for forecourt-fresh new Mini Coopers and Audi A1s. One girl was given a new BMW the size of a small planet for her 17th birthday.

I’m not into cars, I don’t covet hot wheels, I care not for acceleration speeds, sunshine roofs or leather trims. My Sunny was mocked endlessly but it got me and my licenseless friends out from school and into the city, where Real Life took place on Saturday afternoons.

Those showroom cars – though I barely cared about them – brought a sense of comparison into sharp focus. While on a global scale, I’m affluent and privileged beyond belief, in the microcosm of an English public school, I was more orphan Annie than Daddy Warbucks. My dad trained race-horses which is a tough business unless you are right at the very top and he had two kids in private education. It was hard. I wasn’t poor, I was poorer. It’s not a particularly comfortable role to inhabit as a teenager.

There are endless notable, quotable witticisms about money and power. The most apt, I think, is ‘he who pays the piper calls the tune’ although I asked my father what he thought about money and friendship and he said only this: ‘Plenty of people live by the mantra ‘money is like mumps, hang around it long enough and you’ll catch it’.’

Maybe. But while you’re hanging around with money, poor little you is in a state of status anxiety (a term coined by Alain de Botton, the millionaire philosopher). You’re happy to have fun with the rich, but not sure how to pay your share. Because however much fun you are, and however much fun you bring to the party, you’ve got – haven’t you? – to pull some financial weight.

You might, like one writer friend, get lucky and have a film star friend, who takes him to the Caribbean on his yacht; the writer, of course, takes his stellar chum out for a thank you dinner – though the star insists on buying the wine that suits his discriminating palate. (Or you might be unlucky enough to stay at the famously spendthrift Lord Hesketh’s Riviera Villa. Bliss, of course, on one level, but take the Good Lord out for dinner and he’s been known to absentmindedly order an exuberantly expensive vintage, paying scant thought to the state of your pocket.)

I have friends who have much more and much less. I know someone who was given £1 million for their 18th birthday and someone else who currently lives in a shed at the bottom of their grandmother’s garden. Growing up, I was loosely friends with a man who had made Gatsby-eque quantities of cash in his early twenties. People regularly referred to him as ‘the wallet’ – which was fairly loathsome. Then I realised that people did it right in front of him, and he reacted to his nickname with an expression that straddled pity and self-satisfaction.

I can’t help but think of Prince Andrew – not a phrase I thought I’d ever utter, much less write down – and his friendship with paedophile billionaire Jeffrey Epstein. Despite his title, Prince Andrew is nowhere near as affluent as his late pal, who gave the royal use of his houses, jets, private island and even, reportedly, cold hard cash. In exchange, Epstein got to go on a ’straightforward shooting weekend’ or two at Sandringham or Balmoral and enjoy the social cachet of rubbing shoulders with the Queen of England’s favourite son. The reciprocal nature of this relationship which essentially hinged on money and power goes some way to explaining why the Prince found it hard to break ties with the disgraced financier, even after his crimes were first brought to light.

Royals and noblemen have for centuries ‘kept’ a fool or joker as a sort of mascot – someone silly and frivolous – and, crucially, expendable. Guy Pelly, pal of both the Duke of Cambridge and the Duke of Sussex, was when the brothers were teens, often referred to by tabloids and gossips as Court Jester.

The son of a landowner, Pelly, who has an impish baby face and ran a series of nightclubs which smelt like verruca socks and had drink driving convictions, and took the rap for Harry’s cannabis use, was perfectly cast as the rogue whose influence was likely to send either or both William and Harry into another, completely unprincely, dimension.

That Pelly is godfather to William’s youngest son Prince Louis rather puts paid to tabloid smears. Despite how he was rendered, Pelly’s charm was found in his discretion and his sense of fun (he once dressed up as HRH The Queen, which also demonstrates an absence of fawning and a self-assurance in the friendship).

If you are fun – and this doesn’t just mean you like to party until 6am, it means that you can keep your game while partying until 6am rather than passing out dribbling in the dog bed or telling the same story about yourself on an hourly basis – you can get away with an awful lot at weekend parties or group holidays alike.

We all know someone slightly louche who turns up late with an unexpected and incontinent pug but no present for the hosts, often already half cut on Gin-in-a-tin bought at the station but who is instantly forgiven because they are a charming raconteur, a party pied piper, rendering the rest of the guests into servile rats.

It might feel unfair to those who diligently leave a crisp twenty pound note on the nightstand for the housekeeper, or who thoughtfully help load the dishwasher or whose politeness means they are always seated next to the party bore that the person who rides a sheep into the drawing room during drinks, or is found with their pants around their ankles in the larder should be lauded in such a way.

But the fact is, often smart hosts don’t want their guests beautifully turned out as they unload Diptyque Baies candles and bottles of Pol Roger from the boot of their Range Rover. They’d rather someone who shakes things up, even if on Sunday they inhale an entire chicken then say they have no cash for a taxi and could someone just nip them to the station? (Which was, apparently, a trope of a teenage George Osborne’s.)

Out in the sticks, the local Hunt Masters often just turn up at various houses around supper time; the implication being that they have such status they didn’t need an invitation and can’t be refused. They never have to clear up, say thank you or reciprocate.

‘Most of them don’t even have a sodding frying pan,’ said a friend of my mother’s, the morning after the master and his greedy terriers had filled their boots with whisky, wine and Sunday’s leg of lamb.

Often, the rich will find themselves serving as human flypaper for fawning sycophants, while the penniless might feel some kind of pressure to ‘sing for their supper’ when with more affluent pals.

While sob stories from rich people are as welcome as a tooth canal, there is something sad about people who are witlessly used for their cash or connections – largely because they never seem to realise that this is the case. After all, no one wants to admit their friends might only be their friends because of what they can give them in a tangible way. When you are the one receiving special treatment – more fawning, extra attention, more bids for friendship – it is less comfortable to consider that this might be because of what you can offer rather than who you are as a person.

One friend’s parents have an estate in Norfolk which has been the backdrop of many a lost weekend of dancing under the stars in the rose garden and taking midnight dips in the pool. However, said friend Natasha, who is not ostentatious in her manner or dress, is now fully alert to hangers on wanting a slice of genteel paradise that her family home has in spades.

‘Over the years I have detected some opportunists, shall we say,‘ Natasha explains. ‘Lots of people have just shown up with random plus ones who act like tourists. When I was younger I’d be like, ‘more the merrier’ but these days, having had plenty of experience with users, it’s easy to sniff one out. Look for people who want instant connections, access and relationships with you,‘ says Natasha. ‘Real friendship doesn’t work like that.‘

In another instance, Hugo, a music executive working with some of the biggest recording artists in the world, recalls the lengths a potential boyfriend went to in order to exploit his connections.

After a perfect first date of dinner and drinks with no visible signs of madness, instability or foul play, a second date was set up – which ended in bed.

‘After the post-coital cigarette he confessed that he had researched me on the Internet beforehand, found out which company I worked for, which clients I represented and, more importantly, that one of them just happened to be his favourite band of all time, who – quelle surprise – had a comeback show in Hyde Park in a fortnight, and ‘wouldn’t it be nice if we went together on my guest list’,‘ recalls Hugo.

‘For reasons to do with the pain of crippling singledom, I took him to the concert nonetheless, trying to see if the situation was remotely salvageable, but was basically forced to abandon him at a cider stand when he kept going on about how I could get him backstage to get his rare vinyl signed. The sex was awful too.‘

Friendships are both wonderful and difficult; each comes with the potential for lifelong kinship or toxic meltdown. What is true is that when money, power and status are not equal, both parties have a duty to mindful of how this can make a comradeship play out. Nobody wants to be used for their status or money and nobody wants to feel exploited because of their lack of it.

One last thing. A Nissan Sunny is now considered a classic car by Autotrader. I wish I’d kept it and had the last laugh.