One Chicago Sneak Peek: Cast Members Tease Shocking Season of Change

What on earth am I doing?’ I mumbled to myself, pre-date, as I tried on five different outfits in a bid to find the perfect look. I’m 25, attractive – or so my friends tell me – and well-used to the minefield that is online dating.

But this was rather different to the usual swipe, text, meet. It wasn’t about finding ‘The One’ on Hinge among a sea of young(ish) single men. This was my chosen new frontier of dating.

I met him at a Michelin-starred restaurant in West London – a swanky, darkly-lit bistro – where we drank a bottle of extremely expensive wine. He was handsome, smart and great company. At the end of the meal, he paid the bill, ordered me an Uber, and then kissed me on the cheek as he said goodnight.

I left alone – with a purse stuffed full of crisp £50 notes totalling £300.

I didn’t rob him, and nothing untoward happened. In fact, it was the best date I’d had in a long time. It just happened to be with a ‘sugar daddy’ twice my age – 53, to be exact. A Scotsman, on a business trip to London, who fancied the company of an attractive and smart young woman who knew the area. We now have a standing order for whenever he’s down: dinner, cash, company and a catch-up. No texts or calls in between. For a busy girl enjoying being single, it’s perfect – if a bit bizarre.

As many silly things do, my new dating strategy began as a result of both romantic frustration and financial depletion.

Traditional dating apps had begun to feel like a second job, a hamster wheel of repetitive conversations and shallow interactions. I’d spend hours curating a profile, writing a clever biography and choosing the perfect photos, only to be met with low-effort ‘hey’ messages or lewd propositions. Or I’d match with someone, we’d exchange a few pleasantries, maybe grab a drink, and then… radio silence.

Plus the men I was meeting were so often a disappointment. I like to think I’m a reasonably good catch – I’m pretty, a graduate and have a secure job in marketing – but they were almost always boring, self-obsessed or, worse, showed up looking nothing like their photos.

Then there was the financial aspect. Have you ever had a bad date and been stuck with the bill? ‘I’ll get you back next time,’ he’d say. ‘I get paid next week.’

Not that I was expecting entire bills to be paid on these dates (though that would occasionally have been nice); 50/50 would do.

It was never about being cheap – it was the lack of effort and respect.

No, I was finished with diving into the conventional online dating pool. But that didn’t mean I wanted to stop meeting people altogether. I love going to nice restaurants and having exciting experiences.

And so – after yet another unaffordable wedge leaving my bank account, which wasn’t remotely worth the lacklustre company – I sought out other means. A way to date without the disappointment or the monetary strain.

Which was how I stumbled across seeking.com – a website for ‘sugar dating’. Sugar dating is a relationship where one person (the ‘sugar baby’) receives financial or material benefits from another (the ‘sugar daddy’ or ‘sugar mommy’) in exchange for companionship, intimacy or other forms of relationship.

The site caters to all sorts of scenarios: older women seeking younger men; paid-for holidays and a lot in between. Yes, there was some off-the-books sex work, but I just wanted to meet men who were looking to support others in exchange for above-board companionship. No sex for money: I was not going to sell my body.

So I made a profile. Age: 25. Pictures: Solo ones, smiling, at the gym, on holiday, holding a beer -nothing too sexy or suggestive – but all me. I was determined to create a profile that was honest, apart from my name and real job, which was to be given out later if I thought it was going somewhere.

Almost from the moment I pressed the button on it, my inbox went wild. Messages ranged from the simple ‘hey beautiful’ to the frankly bizarre ‘will you be my mommy?’ It was a steep learning curve. I know I sound naïve, but I was struck by just how many men used the site as a kind of escort service.

With a sinking heart, I received a request from a lawyer for a midday hotel meet for £400. Then a chief financial officer asked if I’d be his ‘thing on the side’, after which he’d go home to his wife and kids.

This was not what I wanted. Learning fast, I adjusted my profile and made it crystal clear I would not meet for sex. I was here for traditional dating, companionship and an emotional bond. I soon realised the majority of the bios laid it out simply: ‘Businessman not looking for a relationship, just companionship once a week.’

‘Seeking a girl under the age of 28. Monthly meets. You will be rewarded.’

‘Looking to go to dinner and a show once a month.’

‘I’m on a work trip to London from Doha. Need a spa day with some company.’

‘I’m 29 and I live at home. I’ve never had a girlfriend. I want to learn how to date.’

Some of it, even much of it, seemed too good to be true, like a trafficking or phishing scam.

Someone was offering to send me £600 – which is more than I earn in a week, post tax, in my job – for twice-a-month dinners. Another wanted me to go to Bali with him in three weeks’ time. I didn’t take up the latter offer, but what’s crazy is that most of these messages weren’t scams. The men knew what I was about, knew my ‘no-sex’ rule and were happy to shell out thousands.

And so I started to date. Not once have I been tricked, and everything agreed on upfront has always been delivered, though I tend to ask for as little as possible. Perhaps £100 to pay a utility bill or money toward my winter wardrobe.

For me, it is always still a dating app: I have to like the guy – though maybe not to the same level as on Hinge. So far, I’ve had about 30 dates over the course of eight months. I haven’t ever totted up how much I’ve ‘earned’ – I think that would make me feel slightly queasy – but, as a ballpark, I’d say it’s five figures.

Of course, many messages I’ve received have been inappropriate, despite my very clear boundary setting. I’ve had lots of men – some three times my age! – asking me to be a dominatrix. One man asked me to come to a hotel in ‘princess pants’ (whatever that meant) for an undisclosed fee. These creeps were swiftly blocked.

Again I learned quickly. Finding appropriate suitors has at times been more akin to high-stakes acrobatics than a walk in the park.

Even though I spell out my rules, some still ask for sex when we meet. My reply is always the same: ‘I’m sorry, we must have our wires crossed. This isn’t something I can offer you, but I wish you the best. Can we split the bill?’

A dozen dates have ended this way, and some of the men just don’t understand. They’ve never come across anyone who says no.

Worse perhaps, some of the ‘sugar daddies’ I’ve met were clearly control freaks. There was the man who, on our first coffee date, said I was pretty but suggested I get some ‘cosmetic enhancements’, including liposuction. He said he liked my ‘natural look’, but preferred an ‘enhanced’ one, and was happy to pay for his own Barbie doll.

I smiled, finished my latte, and excused myself.

The thing is, everyone is perfectly honest about what they want, which might be disconcerting but is refreshing too. For my part, I want conversation and a sophisticated time. The odd Uber Eats meal sent to my flat, shopping spree or paid-for bill is a bonus.

It’ll come as no surprise, but living in London in your first job in your 20s is incredibly expensive. You get sick of being so cash-strapped, you’ve nothing left for nice things.

My wages aren’t terrible but I still go to charity shops and batch cook to stay above the bread line – no nice meals out or Zara hauls for me. And regular dating costs. During my fancy dinners or rooftop drinks, I make it clear to the (few) men I’m happy to see again that I have my own life, a career and friends. I am not financially dependent on them. This isn’t a full-time gig. It’s an escape, a temporary detour. I remain in control. And I meet genuinely interesting people.

Take, for example, the ex-pilot, aged 61. He’s flown planes all over the world and has enough stories to fill a library. Now he’s a widower just looking for someone to talk to over a decent meal. At no point has he tried to impress me with his bank account – he just wants to share his life and maybe laugh a little.

We go to gorgeous French restaurants and he tells me about flying Concorde or having celebrities on his planes. And, if he’s lying about his fantastic stories, who cares? I’m being wined and dined and having a great time.

Plus, when I complained about my tax bill, he started sending me a couple of hundred quid by PayPal every few weeks. In April, with my birthday coming up, we went to an even more gorgeous restaurant than usual.

Another longer-term situation was the shy tech guy, aged 29. He was smart, but when it came to dating, had no idea. He just wanted a friendly companion to teach him the ropes – someone to make the experience less terrifying. He showed up in a suit, with flowers, for an afternoon ramen date, which I later teased him about.

We spent the evening laughing and talking about everything from video games to bad movies. He was surprisingly normal and just needed some confidence.

When he felt ready to graduate ‘dating school’ he gifted me £500 wrapped up in a bow as a thank you, despite our previous agreement simply being that he would always pay.

And I can’t forget the divorced dad in his 40s with too much time on his hands. He got a thrill out of spoiling someone young like me – a recent graduate still paying off her student loan.

He wasn’t looking for a ‘mutually beneficial arrangement’, as is often described on the app for those seeking escorts, just the joy of seeing me light up when he bought me something I’d only ever dreamed of – the designer handbags that had been on my wish list for ten years, or the dream console table for my flat. I had a monthly flower delivery from him – huge bouquets of seasonal blooms. But it was less about the gifts and more about the fun. We went out for gorgeous dinners, had spa days and enjoyed a good time.

I know it sounds naïve – and at the start I was braced for a question I’d have to bat back – but not everyone is after something else. All he wanted was an attractive companion. He didn’t need a second wife, or a step-mother to his children, just a distraction from the daily rigmarole.

I like to characterise this dating strategy as having a good time with interesting people who just happen to be incredibly generous. And the ‘right’ men give me much more than I’d expected. They’re kind, respectful and fun.

Of course I am always uber-safe. I go into every first encounter with ground rules I decided on during my trial-and-error phase. First, I only meet in a public place – a crowded restaurant or popular bar – never a hotel room or a private residence.

Second, I don’t engage in any conversation that makes me uncomfortable. If the vibe shifts, I am always prepared to leave, instantly. In those early days, I often did. Third, and this is a big one, I won’t date anyone older than my Dad, who is 65 next year. And finally, I won’t see men who have wives or girlfriends – I’m not a mistress.

Yes, friends tend to roll their eyes when I describe my sugar daddy dates. I’ve been told it’s risky, stupid and unnecessary – and the naysayers aren’t wrong. But for me it’s a fun escape.

I still get weird messages, dodgy situations I quickly head out of and monthly existential crises, but I’d have all of that dating on the conventional apps.

So what’s the harm? This side hustle is a moment of freedom, not my long-term plan. I’m under no illusions that I’ll marry a rich man from this site. I know this is a whirlwind while I’m still young and pretty. But honestly, it’s more fun than splitting the bill on another lukewarm coffee or overpriced pint.

Does that mean it’s for everyone? No. But it is my cup of tea and so long as it continues to be served in a fine china cup, I’ll carry on drinking.

Sarah Hall is a pseudonym.