Date Diaries: The First Time Sugar Baby At Drinks With A Christian Grey Wannabe

Date Diaries is a series chronicling the anonymous adventures of those involved in the ever complicated and increasingly unbelievable world of modern dating. To submit your story, fill out the form at the bottom.

This week, Amy a 26-year-old heterosexual graphic designer from Essex meets a man who bases his entire personality on romance novel cliches...*

First of all, let me start by saying this was not my typical date. Meeting a stranger from Tinder? Sure, that’s just Friday. But a sugar daddy date with a man off Seeking Arrangement? Not likely.

I met Christian – not his name, but he would love the reference – on the sugar daddy dating app just days before we arranged a date. I’d made a profile on Seeking Arrangement when I was a student, but more as a laugh than anything. I never really took it seriously until about two years later, living in London and very broke.

It was the old ‘friend of a friend’ tale that seduced me. ‘So this one girl I know meets this guy for dinner once a week, he gives her £300 every time literally for just talking,’ one of my girlfriends told me over drinks. Naively, it sparked a thought – why don’t I just try and take the app seriously see what happens?

So I went about chatting to various men, hoping to find someone I would actually want to date anyway – then, the inevitable conversation about sex wouldn’t be so awkward. That’s when I saw Christian. He was 34, handsome and a property developer. His profile made him sounds charming, and on Seeking Arrangement, that’s like finding a needle in a very old, very creepy haystack.

His profile mentioned something about liking submissive women, but I shrugged that off given he was the best of a very bad bunch. After all, there are no hard and fast rules about sex in the sugar baby community – some have it, some don’t. Ironically, that vagueness makes for much more awkwardness later on.

Over direct message, Christian got to the point very quickly: he wanted to take me out for drinks and was willing to pay £100 for the privilege. That’s where I was sold, literally. From what I’d read online, paying for the first date with sugar babies was not the norm. Typically, it’s the ‘getting to know each other date’ where no money changes hands unless an arrangement is agreed. ‘£100 for a drink? What’s there to lose?’, I thought. My faith in men, I would come to find out.

After we swapped actual numbers, Christian asked me to meet at a hotel bar in central London. The choice of location made me wary about what he was expecting, but he suggested a Sunday afternoon and I relaxed slightly. ‘Fuck it, I can take his money and run if it gets weird’, I thought to myself.

Getting ready for the date, I have never felt so out of body. Normally I might be nervous for dates, but this was like going for a job interview. The money (and potential arrangement) upped the ante substantially, I already felt unsure of the power dynamic I was walking into.

Looking back, I was naïve, I convinced myself that just because he was paying me doesn’t mean he would treat me any differently. How wrong I was.

My first clue came on the journey there. He’d pushed back the meeting time to hours later, which I was fine with. However, when I requested the same courtesy, he responded a stoic ‘ok.’ Then, as I walked through central London to meet him, trainers on and heels in my bag, he told me he was running 40 minutes late.

So I sat waiting, for 50 minutes in the end, watching the door and frantically texting my friends asking whether or not I should run. When he arrived, I instantly regretted not doing it. Spotting me sat in the brightest area of the bar, he walked straight past my table and signalled for me to follow him.

‘Okay, weird but fine’ I thought as I diligently got up and walked over to the sofa he was now lounging on. It was in the darkest corner of the room, but I already could see he was a lot more handsome than his pictures online.

Beckoning me to sit on the same side of the sofa as him, I perched politely as we began to exchange pleasantries. But that tone he had set by ordering me to move tables without even saying hello only grew stronger. First, he complimented my green midi dress and asked me to get up to show him it properly. I did, because it was awkward, but I attempted to turn the conversation from comments on my body to how versatile midi dresses are across seasons (lol).

It didn't work.

‘You’ve got hamstrings haven’t you,’ he said, reaching over and grabbing the back of my thigh. ‘Thanks, it’s nice you feel so entitled to touch them,’ I replied snarkily. Already, we seemed to have entered into a delicate back and forth where he was testing how much control he had over how I act, and I attempted to assert some dominance with sassy remarks.

Our conversation started with work chatter, during which I tell him I think all property developers are probably sociopaths. He laughed me off, all the while sniffing and snorting uncontrollably in a way that makes you wonder what’s up his nose.

Then, as we naturally turn to politics (God knows why this always happens to me), he started explaining why men are the superior species. You know, biologically. I sat, smiling in the most patronising way I possibly can, and he caught on. ‘What do you think about that?’, he asked me. ‘I think that’s complete bullshit.’ I replied, beginning to explain why.

It was very obvious, from his words and his behaviour, that his view of women was not going to change from a conversation with a 23-year-old he’s paying to have drinks with. But I tried. Then, all of a sudden, he decided he’s hungry. ‘I’m going to order food, and we’re not going to be able to talk while I eat, so just play on your phone,’ he demanded.

Lo and behold, when his steak arrived, he stopped speaking completely and began gorging like a caveman. I excused myself to the toilet, and when I returned, I had no choice but to do exactly what he said: play on my phone.

An hour into our date, the red flag I should’ve seen when he was 50 minutes late caught a new wind. ‘So how come you pushed back the time?,’ he asked in a way that told me he is not normally the one compromising his time. I explained why I was busy, and made a comment about his lateness. ‘Well, you should be the one waiting on me,’ he declared.

As we finished our third drink, we entered into the ‘arrangement’ chat. ‘My last arrangement, she would come to my flat once a week and I would give her £150, how does that sound?’ he asked. Somewhat taken aback by both the sudden offer and price, I told him £150 is quite the bargain for a weekly arrangement. ‘Well, she liked me anyway so the money was just a bonus,’ he said.

‘Ahh you see that’s the thing,’ I smiled, ‘I don’t like you.’ He laughed, of course assuming I’m joking.

When the date was finally drying up, he announced with sudden urgency that he’s going to leave. ‘How much did we say, £100 right? I just need to go to the cashpoint,’ he told me.

At this point, my head was spinning from batting off so many conceited comments and uncomfortable orders that I wait patiently as he leaves. The waiter approached with a look that tells me he’s worried about me and I smiled at him in reassuringly, although I no doubt looked dead behind the eyes by now.

A few minutes later, Christian returned with the cash (‘did you think I’d just got off without paying you?’ he laughed). He hugged me goodbye and says he’ll be in touch. ‘Yeah, I’ll let you know if I want to see you again,’ I said politely, thinking nothing off the casual goodbye. ‘No, I’ll let you know if I want to see YOU again,’ he urged.

I couldn't help but laugh as he left. This man, so dominant in every sense, was so dreadfully insecure. His aura reeked of Christian Grey lite, someone who gets high off controlling women but can’t actually pull off the sex appeal that’s meant to come with it.

Walking home, I felt both exhausted and exhilarated. ‘Never again,’ I told my sister on the phone. I may’ve thought this would be a quick and easy £100, but alas, I definitely earned it.

That was my first and last sugar baby date, much to his dismay. Despite all of his wannabe superiority I got the last laugh when he text me the next day saying 'Hey x' and I read and ignored it. Sorry Mr. Grey, Anastasia will not see you now.

As much as I’m sure there are eligible sugar daddies out there, for me it turns out that even when you find the needle in the haystack, you still end up with a prick.

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