Grapeshot Challenge: How To Lose A Sugar Daddy in 27 Minutes


Words || Nikita Jones

This is by far the stupidest thing I’ve ever done, and I’ve done some stupid fucking things. I’m walking through the restaurant watching long grey hair flop on his shoulders as he bounces up to the counter to order. With his back to me, I chance a quick glance at my strategically positioned friends whose expressions are not at all comforting. Among them is my predecessor, Phillip, whose journalistic legacy of doing dumb shit in the name of Grapeshot I am attempting to live up to. Last year he got a tattoo of his own face, posed as a nude model, and ate nothing but Vegemite for an entire week and here I am, shivering over a paid meal with an older gentleman.

Girls do this all the time, I know, I had enough trouble finding a username for my profile to determine that there are least three separate women named ‘Nikki’ born in 1996 who prefer the paying company of an older man. However, my particular personality – sort of prudish, overly picky, and to be honest, pretty gay – is not conducive to this lifestyle in the slightest. There are very, very few older men I would consider dating for even a moment, and all of the ones I would consider have Oscars. Unfortunately, a yacht on Sydney Harbour just doesn’t quite sweeten the deal enough to make me swallow my own bile.

Admittedly, the earlier stages of this challenge were quite fun. After wincing through creating the most potently naïve and bubbly bio this side of believable and enduring a candid (staged) photo-shoot by the pool (not mine) with a cocktail (warm cordial in a nice glass), I left my profile to settle. I didn’t even have to do anything, 13 new messages rolled in within a matter of days. Without any preamble, I was offered $200 cash, a flight to Melbourne or Brisbane (shopping trips included), and a night at the Four Seasons, all from different men. And this was on a light membership, who even bothers with the Gold? I picked ‘Paul’ for literally no other reason than that he was available at a convenient time for me.

So after all that came the grossness. I’m no stranger to pretending to listen to old white men – I don’t think there’s a woman in the world who can say she’s never suppressed an eye roll or fixed a polite smile – so I figured this would be the easy bit. As it turns out, what I am a stranger to is deflecting overtly sexual propositions and questions.

“Are you interested in an intimate relationship?” Not with you. “I’m looking for someone who will take orders.” I think the waitress is on her way. “What do you like in the bedroom?” Someone who isn’t roughly the same age as my dad.

Before sinking myself into this hole, I’d devoured quite a lot of media on the Sugar Daddy/Baby lifestyle, from insipid Daily Mail articles and Sunrise segments to personal blogs and testimonials from the University of Sydney’s many sugar babies. The former tended to wax paranoid on the explosive phenomenon of shallow teen girls seducing wealthy older men into handing over their cash, which surprised me zero. But the latter had a more authentic handle on the actual nature of these relationships and they almost exclusively amounted to a sentiment of: sexual commodification equals sexual empowerment. And for those who have stuck by the Sugar Baby lifestyle, I don’t doubt that’s the case. From my own personal experience, I can now say that it’s gotta be more than money that makes this worth it, and sexual empowerment seems as good a reward as any.

Only three minutes into our conversation, and I’m so thoroughly averse to pretending I want to have sex with this man that I start going full Kate Hudson on the poor guy.  I’m not sure what it is, maybe a defensive instinct, or insanity under pressure, but instead of proceeding with our date in a reasonable way, I start inexplicably throwing my personality to its furthermost undesirable edges.

“Tell me about you,” he says.

I can’t seem to settle on one unattractive trait so I’m at once antagonistic, dumb, vague, and sarcastic. I ask him about politics around five minutes into the conversation, fly to the defence of Meryl Streep and Jane Austen, accidentally start some gender discourse, and reveal my distaste for fine dining – which, coincidently, is one of his fondest passions, behind adolescent girls. When the food arrives, I shove the entire burger in my face and escape to the bathroom to arrange for my immediate escape.

27 minutes later – I have the timestamps on my “pls help” text messages to prove it – I’m purging his entire existence from my mind with ice-cream, red wine, and the kind of friends I trust as spotters for a date with a Sugar Daddy.