A few years ago I wrote an entry level article about researching the world of Seeking Arrangement sugar babies or ‘sugaring’ in the Waikato. It had some pretty easily hypothesised conclusions: Waikato had no rich talent and all the would-be sugar babies I spoke to were creeped out and generally disillusioned by their experiences on Seeking Arrangement.

 

Back then I didn’t really feel like finding one of my mates’ dads online, so I didn’t dip my toes in nearly enough. This time around, I decided to get a bit more journalistic.

 

Let me set the scene, it was pre-pandemic London; a thriving metropolis of genetically modified super rats, class systems and old coloniser money, where Sugar Daddies are as plentiful as guys trying to give you their mixtape on the tube. However, the market is competitive. A mutual acquaintance of mine got holidays, business class flights and bags of coke all over America with her Daddy. My flatmate was offered an outfit, shoes and perfume of her choice for a first dinner meeting. No strings attached. In a city of millions, where I know approximately ten, what can go wrong? 

 

Don’t answer that. 

 

This time around I was unemployed and had plenty of free time, so I reactivated my Seeking Arrangement account and went on my merry way to rewrite the story. The experiment was simple: I would go on one date and write a sequel article.

 

Which led me to my first (and spoiler alert last) date; a 40-year-old (with no public photos on his account) named Sam*. He seemed normal. We talked on the phone for five minutes and it wasn’t weird – he was super nice. He worked as a professional recruiter and consultant for four businesses and wanted to help me find a job. He asked if I was free for a quick drink to see if we would get along – he also said he’d had two relationships from SA before and neither of them had wanted money because they felt it was ‘real’. In hindsight this should have been a major red flag. Rule #1 of Sugaring: Get the sugar. Your eye must remain firmly on The Bag. 

 

I stressed about what to wear for an hour, messaged three friends my whereabouts, put my location on and made my way downtown. Rule #2 of Sugaring: Have an escape plan and check in with your friends.

 

About one minute after I got off the tube he asked if we could postpone it by 30 minutes because his client meetings were running overtime. So I sat outside the busy train station taking calls for job interviews, anxiety skyrocketing for an extra 27 minutes and then made my way to the meeting spot. It was a fancy bar in a 5 star, very well known hotel that rhymes with Bitz. I perched at the bar in clear view of all the staff and patrons (safety measure) and told the bartenders I was waiting to meet someone. 5.30pm rolled on, I got another text: “I’m so sorry baby, I’m running far behind, be there in 10 xx” I was starting to feel fucking creeped out – he was calling me baby and ‘xx-ing’; was he already here and watching me? Was his fetish standing people up? I employed the avoidance strategy learned from years of experience ghosting Tinder boys and texted back: “I have to meet a friend soon, maybe we should postpone?”

 

He immediately called me, “So sorry! I’m just paying now, I’ll be there in less than 10, even if we can only meet for 15 minutes.” Okay, I could do 15 minutes. I needed some firsthand experience, for journalism. Journalism, I tell you!

 

When he arrived I couldn’t quite believe he was 40. He was the old man equivalent of a 5’9” fish-holding tradie on Hinge who says they’re 6’0”. I was more sexually attracted to the Art Deco interiors in the bar at this stage but I wanted at least a free drink and to figure out if I could get some money off him. Maybe I’d have to mug him. 

 

Convo started casually, and then shit got weird. 

 

“Did I tell you on the phone about dresses and skirts?” He said, looking ponderously into middle distance. He’d informed me he never drank but his meetings had been wine-related so ya boy was more than a little tipsy. 

 

“No,” I said, you absolutely did fucking not sir. He told me that he was always worried the girls he was going on dates with were journalists. I felt zero guilt. Oops.

 

He asked if he could whisper it to me and I was starting to feel like I’d sold part of my soul.

 

“My kink really is the age gap,” he admitted, after he went on his 5th tangent and I had to click in his face and say “DRESSES AND SKIRTS” to get him back on track. 

 

 “I love the idea of you being virginal or at least less experienced…” Okay bro, well you obviously didn’t see me at Static in first year. 

 

“I don’t have any children and it might be slightly Freudian, but I like what I can teach you.” Weird. 

 

“And I love seeing the difference between men and women in meetings, skirts versus trousers.” Firstly, that’s sexist, and let me say at this point – I was wearing pants. I think I look cool in these pants. They’re nice pants. 

 

“And the most turned on I think I’ve ever been…” He was no longer whispering in my ear, but instead saying rather loudly one foot away from the attractive bartenders, “was in a client meeting, when an associate of mine uncrossed her legs and accidentally flashed me her white cotton panties.” 

 

WHITE. COTTON. PANTIES. 

 

This was a first date, the dude wasn’t cute, I wasn’t getting paid and he was already fucking creeping me out with his manipulation techniques, child bride fantasies and inappropriate unsolicited fetish talk. Needless to say I bolted. Tactfully. I excused myself and said I had to go meet that aforementioned friend. Adios. I left him to pay the bill and wallow in white cotton panty related arousal and got in an Uber straight to the bar my friend was working at to regale my tale and pay for my own drinks. He tried to call me the next day and I blocked his number and never spoke to him again. 

 

Now, upon reflection I made a lot of wrong turns with the monetary side of things, I ended up with a good story, but out of pocket an Uber ride and tube fare. And there’s a lot to unpack here; I feel no shame for attempting to turn my free time and charismatic nature into cold hard cash and a decent piece of writing, but I think we can all learn a thing or two – daddies, mummies and babies alike, from my experience. So here are my top five tips for the aspiring sugar baby.

 

  1. Get the sugar

This absolutely goes without saying. My politeness got the better of me and I forgot the most important factor in a transactional date – make sure there’s a transaction. If someone tries to manipulate you with a ‘first date free’ card, drop them. Or as Fergie says, if you ain’t got no money, take yo broke ass home.

 

  1. Be safe

I did this one well. Fortunately, I ran into nothing super concerning, but I’d prepared for the worst. Turn your location on, let several people know where you are, go to a very public restaurant, have an escape plan, use the staff as a safety net. You can even create yourself a sugar baby persona.

 

  1. Don’t think that you have the right to be inappropriate 

This one’s for the daddies and mummies. Just because this is an arrangement does not mean you can bring up unsolicited, uncalled for conversations. Fuck off with your Freudian bullshit on the first meeting. I’m not kink shaming, but this kind of thing is to be negotiated, not dictated. 

 

  1. Set and manage expectations

Both parties need to be straightforward. The first meeting can be a vibe check for sure, but anything further needs to be set in stone. If you misrepresent your expectations, you’ll never be fully happy with your arrangement.

 

  1. You are in control

Unless this is a dom/sub scenario, in which case, LESS power to ya, never forget that you are the captain of your fate. Say it with me now. You call the shots. This doesn’t mean being a judgemental asshole, but don’t let anyone manipulate you or make you feel like you deserve any less. Now fly, my sweet. Go get yourself a Gucci bag