Why You Shouldn't Date Rich People if You're Broke

I don't earn much money. This is a problem, because as I've got older my tastes have grown more expensive while my income has remained the same. When I was 15 I was able to have a great night out with just a ten-deck of fags and a bottle of Frosty Jack's (£10). As a student, all I needed was a pinger and entry to a club (£20). These days, I like small plates restaurants, Scandinavian workwear, living in east London and other substances (£???).

Given I can barely afford any of these things, it would make sense to find some rich sucker to foot the bill, right? Wrong. When you're broke, it's easy to be taken in by the fantasy of fucking your way to the top, absorbing someone else's money by osmosis. Having dated a string of rich men, however, I've realised that this strategy rarely works. At least, not outside of Victorian novels or the music of Lana del Rey.

Here's why.

Rich people can do whatever they want (they could go to Burger and Lobster and order both burger and lobster!), so why would they choose to spend their evening eating at a Wetherspoons in Brockley and listening to you enthuse, with increasing desperation, that the curry is actually surprisingly authentic?

People who earn a lot of money – all of whom have the word "ambitious" in their Tinder bio – tend to look at prospective romantic partners as a financial investment. In ten years, they want to own a house in Ibiza. The best you can hope for in a similar timeframe is not being priced even further out of Peckham. As far as safe investments go, you’re hovering somewhere between Dogecoin and a "music technology" startup run by a Goldsmiths graduate.

But would you even want to date a rich person anyway? For Lily, a 25-year-old who lives in London, the answer is a firm no: "This is a massive generalisation, as all the best statements are, but every properly rich person I've met has either been extremely dull, had politics that clashed with mine past the point of 'friendly debate' and straight into the realm of 'to the gulag!' Or both."

She continued: "I'm yet to meet a rich person who makes me laugh. Or is good in bed and doesn't just see a woman as something to pump away at for a few uninspiring minutes before collapsing on top of you in a move so cliché it could have been pulled from a 1990s Jo Brand routine. Yes, Tinder Daniel, I'm talking about you."

So fuck 'em!

Any personal relationship entails a level of financial give and take, the assumption of a reciprocity that will balance itself out without having to hire an accountant. Curiously, people with the most money are often the least equipped to handle this. It could be a wealthy friend buying you a pint then asking you, the next day, to Monzo them £5.75. It could be a partner keeping a tally of everything you spend together then hitting you with receipts (maybe literally) if the numbers don't match. It could be your landlord selfishly demanding half of your wages each month, despite the fact they own 15 houses .

So why are rich people such horrible, stingy bastards? Does it stem from a perhaps understandable prickliness surrounding being taken advantage of? Is their frugality the very reason they have so much money in the first place (or the reason their parents do)? A few of the people I spoke to suggested this, but, as an explanation, it sails too close to assigning wealth a moral value: people aren't rich because they're frugal any more than people are poor because they're feckless. So is the reason simply, as one friend put it, that rich people "are grasping hoarders of wealth who believe they deserve what they have, and tough shit to anyone else"?

Being with someone who pays for you can create a sinister dynamic. Last year, a man I’d only been seeing for a fortnight asked me if I wanted to come with him on a work trip to LA. Despite realising this was a stupid idea, I knew that I would never able to afford to do it myself – so I said yes. At quite a vulnerable time in my life, I was flattered by the attention of someone so successful, someone who would bombard me with compliments. When he said things like, "You're utterly singular," I convinced myself that I liked him. Not long after we landed at LAX, I realised this wasn’t the case.

For a week, we ate stuffy, overly rich meals in the hotel restaurant, visited the same private member's club he belonged to in London, took too much coke and spent the daytimes sleeping it off. I often found myself thinking, 'This should be fun,' and blaming myself for the fact it wasn’t. I felt like a character in a Bret Easton Ellis novel, disaffected by luxury in a way that was as boring and cliché as, well, a Bret Easton Ellis novel. I realised I would have had a far better time at a Travelodge in Plymouth if I’d been with someone I liked.

The sex was strained, too. I no longer found him attractive, but I felt obliged to sleep with him since he’d brought me there, since I hadn’t had to pay for anything. It's not a great feeling consenting to something you don't want to do. To make an obvious point: there’s nothing degrading about sleeping with someone for money. But sex work is work: dating someone because you enjoy the lifestyle it affords you isn’t – which makes it harder to set boundaries, harder to stay in control.

On our last night, at a party, he cornered me in a bathroom and tried to persuade me to have a threesome with a man we had met. I told him I didn’t want to but he kept pushing it, accusing me of "ruining the holiday"’ He succeeded in making me feel like a spoilsport – ungrateful, even – but I finally told him to fuck off with sufficient force that he dropped it. I ended up having a panic attack on the taxi ride back to the hotel and lying awake until it was time to catch our flight. We didn’t say a word to each other until we arrived back in London, where we said a cold goodbye and never saw each other again. It was, without doubt, one of the worst experiences of my life.

Still, though… LA!

One of the rich men I dated had a lifestyle so glamorous that the envy began to eat away at my soul. He was, quite simply, always on holiday. I would be working in a pub, sneaking away when it was busy to send him nudes from the cellar, surrounded by cobwebs and exposed wires. He in turn would send me pictures of himself lounging on deck chairs and drinking expensive health juices; five-second clips of him shouting "tuuuune!" at open-air house nights by the sea. I began to feel bad about how shabby my own life was next to his.

This was someone who could take out his phone at a bar, scroll through a menswear site, see a £500 jacket he liked and just… buy it? As a profoundly stylish but broke man, I still consider this a grave injustice. You can’t even conceive of how well I would dress if I had more money. The sheer, monochromatic tastefulness… it’s beyond your imagination.

So although I’m not bitter in the slightest, I do find myself wishing for a revolution in which every single item of Our Legacy clothing this man owns is violently expropriated and then given to me, personally. That’s what communism is all about.

Over the past week, a Twitter debate has raged over whether dating rich men constitutes good feminist praxis. As a man, I understand it's not my place to make pronouncements on this issue. So I asked Lily, a woman, no less, for her thoughts.

She told me, "This trend of believing it’s somehow admirable and powerful to rinse a man for all he’s got is so tiring, especially when people try to defend it through a feminist lens. You are not empowering yourself by dating men for free stuff. It’s still a dependency. The capital is still in someone else’s hands."

Lily, too, thought there was an important distinction to be made between this kind of relationship and sex work: "Unlike sex work, which is defined by the boundaries of a business transaction, every instance I've seen of people trying to 'scam' men usually involves them adhering to their every whim in exchange for the floated promise of cash that may not even appear. There's no terms. Your dignity is the price." She added, "Cardi B is the idol of the 'secure the bag' brigade, but guess what, guys? She secured her own bag. In fact, her husband is a hindrance, not a help."

If you’re broke, it's easy to think of shagging someone rich as redistributive, as justice of a kind, and maybe in some cases it works out that way (I’d never judge anyone for giving it a go) – but you need to be honest about where the power lies. Although the gender politics are different, the LA incident outlined above is an example of this dynamic turning sour: I may have thought I was "getting the bag", but in the end all I was getting was sexually harassed in a toilet.