The men who pay for love

Inside the world of Seeking Arrangement

“All relationships are transactional,” Amy says. “This is just being up front about it. I think that’s why some men like paying for it. They know what they’re in for from the start.”

She then takes a sip of her cocktail — it’s extravagantly fancy. Filled to the brim with ice, decorative flowers and luridly-coloured alcohol. I had opted for a martini.

I nod, but I’m not sure I agree. How could men possibly know what they’re in for with Amy?

She is, of course, gorgeous. Young, tanned, blonde, big lips, and an enviable figure. We’re socially conditioned to assume these traits come at the expense of intelligence. But Amy is no fool.

A few years ago, bored by the monotony of her work, Amy decided to make some cash on the side. A friend recommended that she tried using a website called Seeking Arrangement (now just called Seeking). For women, the service is free. Men are the ones who have to pay.

And pay they do.

For $110 a month you’ll get full access to the website.Then if you match with a woman you like, and come to a mutually acceptable agreement, you’ll pay to date her. In almost all instances, that will mean sex. But you might also be up for nice dates, shopping allowances and a weekly upkeep. It depends how deep your infatuation and pockets run.

I ask Amy to let me have a go on the app, she passes her phone across the table.

I hold my drink in one hand and her mobile in the other as I swipe through the profiles of prospective suitors.

An older man, in his 60s perhaps, sits in a garden. He’s wearing a faded blue polo shirt. He isn’t smiling in the photo, and has deep lines etched in his face, like someone who has spent a lifetime working in the sun. It’s obvious that he’s snapped a selfie in his backyard. I swipe no.

The next profile belongs to a young man. I think he could be a tradie, stocky, tanned, and wearing high-vis in a couple of his photos. He also uses unsmiling selfies, but has at least has one group shot with friends. They are an amorphous herd of nuggety men with buzz cuts.

I keep swiping.

“None of these people look like they have money,” I say.

Not that money looks the same for everyone. Custom-made suits, yachts, and trips to the Amalfi Coast is just one expression of wealth – the kind we see in magazines and on television shows. There’s also corporate money, small business money, trust fund money, drug money, new money, dwindling old money – each with their own specific tells.

In my many years of working in the media, and generally courting interesting people, I’ve encountered them all.

But these guys, who I’m flicking through quickly on someone else’s dating app, just look like ordinary men. The kinds of blokes you’d swipe ‘no’ to on Hinge, Tinder or Bumble. Maybe that’s why they’re here.

“There are a lot of time wasters,” Amy says. “You’ve got to spend a lot of time filtering them out.”

That happens in the form of long online conversations. There’s no meeting for coffee or chatting in person — that would come at a cost. Amy is clear with her expectations.

She sends them a list of services, and how much they cost. ‘You can take me out for dinner for this much. You can sleep with me for that much. If you want me to stay the whole night, it will cost you this’.

Clear communication is important in any relationship.

None of the profiles on the app looked like this bloke.

I went on a few dates with a very rich man once. We matched on Tinder and struck up a conversation about cars. In one photo he was sitting in a Porsche — I assumed it was a rental, or belonged to a friend — but I didn’t ask and he didn’t say otherwise. His name was James.

James and I had loose plans for a casual Sunday date, but then both of us got extremely drunk the night before. We texted back and forth, threatening to cancel, laughing about our shared predicament. Eventually, we bravely decided to go for a walk.

We met at the Bondi headland and then ambled south along the ocean path. I was pasty, puffy and sweating last night’s booze through my pores. James didn’t look much better. But the conversation was lively and fun anyway, so we decided to keep things going and get dinner.

“Have you ever been to Mimi’s?” he asked as we arrived at Coogee.

I hadn’t, but said it sounded good. I assumed we would be going to a cheap-and-cheerful local pub. In fact, it was one of Sydney’s more expensive restaurants. It didn’t take me long to realise. The people at the tables around us were well-dressed, and had clearly been preparing for a special meal out.

We were just two supremely hungover pieces of shit.

I expected to be politely but firmly escorted from the premises. The woman at the door immediately recognised who I was with.

“You’ve been here before, haven’t you?” she asked.

“I have,” James replied with a slight smirk. “I’d like a table with a view,”

“That won’t be a problem,” she replied. “We’re just finishing up with lunch service, but let me take you to the bar while you wait. We’ll send the sommelier over.”

Within moments, an elegant young man arrived and presented a different menu to the one that was on the table. James chose a bottle of wine towards the back of the pages and by the time the table was ready, I was once again drunk.

Realising that splitting the bill would leave me destitute, I asked James to choose what we would eat. We ate “caviar bumps” (served on the flesh between my thumb and forefinger as though it were cocaine – a crass bit of Eastern Suburbs food theatre), several plates of exotic entres, and steak that was so expensive it warranted a personal introduction by the head chef.

By the end of the night, we had shared more than two bottles of wine, a large amount of food, and I was seeing double. James — who it transpired had made a fortune from a cyber security company — was openly vaping at the table.

But no one was stopping him. Perhaps, because the bill came out to be over $6,000

I would price the subsequent two-day hangover as around $12,000 of pain.

I only met up with James a few more times after that – I knew it wasn’t going to be a forever thing. He was a busy man preoccupied with his own, complicated life.

But even if it did work out, how could anyone feel comfortable with such a power imbalance?

James was younger than me, in his early 30s, and rich in a way I struggled to comprehend. Meanwhile, by all measures, I am a fairly ordinary person.

I did ask once why he didn’t date beautiful influencers – we both lived in Bondi at the time, where they are a plentiful resource.

“I hate gold diggers,” he’d told me. “They just ask me to buy them designer bags all the time.”

Clearly I was out of my depth. When James had been on a holiday in Japan, he asked if I wanted anything. I requested a stupid souvenir and was thrilled when he gave me a large dumpling-shaped pillow.

I should have asked for a Louis Vuitton handbag.

That was one of my last conversations with James. The momentum stuttered, the text messages slowed, and then eventually stopped altogether. I had been a brief tourist in his life, but wasn’t sad to go home.

When it comes to relationships, I ask very little, expect slightly less, and am still often disappointed. Sometimes I think I prefer it to the horror of truly being known. Cracking open one’s sternum, prying apart the ribs, and revealing your vulnerable inner core and all its desires is surely an act of madness.

Does Amy have such qualms? Certainly not when it comes to asking for material things.

She’s been flown to exotic locations for all-expenses-paid holidays. She’s drunk champagne as old as me on private terraces with ocean views. I suspect at least one of Amy’s men has sent himself broke – or close to it – trying to please her.

We finish our dinner, Amy and I. We then meet another group of friends at a bar. When it’s late enough that the busses aren’t running, I decide to go home and sleep.

Amy gets an offer to see a man – she’ll get a thousand dollars for spending a couple of hours with him.

“My missus is going soon,” he’d texted her. “I’ll send a car when she’s gone.”

We both head outside together to wait – Amy insists on paying for my Uber home. At first I refuse her offer, but she eventually wins by biting me on the arm.

“Let me do something nice for you!” she shouted at me while I laughed.

The next day I wake up with a bruise on my arm and a lingering anxiety. Was Amy okay? I reached for my phone and fire off a text message.

“How did you go?” I ask.

I don’t have to wait long for a response.

“Great. Got a grand for chatting shit for an hour and a half,” she replied. “No sex just kisses.”

Are all relationships transactional? Is love something that can be put on scales, measured and priced? I’d like to think that’s not the case. But if they are, one thing’s certain – some people are better at negotiating terms than others.