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rich, lonely men paying my rent

Imagine this: you’re in a house by the beach, the rent is paid, and you’re lounging on a feather-stuffed futon in a silk robe. You delicately shovel caviar into your mouth from well manicured fingertips, and sip a glass of champagne. Your antique clock strikes seven — it’s time to meet your gentlemen friend for dinner. So you slip into your Porsche, which is insured and paid for in full, no car loan required, and head to the Bellagio where you’ll meet him in the bar for pre-dinner drinks.

This is how I like to think life looks for women who sign up to sugar daddy dating sites, and this is the image that came to mind while I was reading one of those tell-all style, “I’m financing my life by dating rich dudes,” articles this week.

According to the woman in the article, Rose Clifford, she’s earning more than $13,800 a year by going on dates with CEOs, directors, and other high-flying, career oriented and terribly lonely kinds of guys.

“Each time we met he gave me $260 and if I ever needed money whilst he was away he would transfer me $325,” she says of one of her regulars.

“Usually men offer $170 to $260 per date,” — BUT, get this — “I’ve had offers of $8.50 before.” That’s not even worth the makeup you’d put on.

Now, usually, this would just be something I would read, laugh at and then forget. But here’s the thing — I’ve been on the hunt for a secondary source of income for a while now. I considered investing, or buying lotto tickets, or selling arts-and-crafts on Etsy, but none of them quite have the lazy-appeal of being paid to go out to dinner.

So, in the interest of exploring all possible avenues of personal finance, I’ve done what my mum always said I should do when faced with a tricky decision and made a list of pros and cons. I don’t think she ever expected me to use her advice to decide whether I would date rich men for money, but hey, life’s weird.


  • I will no longer have to pay my rent. This will give me disposable income that can be donated to charity, spent on furthering my education, or sunk into the financial black hole that is my preference for fruity cocktails.
  • A chance to buy a house. I don’t know if you guys know this, but it’s next to impossible for young people to buy a house in the current Sydney market. I know I’m light years away from home ownership. But Clifford says she’s well on her way.
  • Wealth re-distribution. The money these rich guys spend buying me dinner will go to pay wages for the waitstaff and dishwashers. I’m contributing to the economy.
  • I won’t lie — I am interested in scoring a pile of designer stuff. At the very least, I could re-sell it on Ebay for a tidy profit.
  • The more money these guys spend on me, the less likely they are to spend it on dumb stuff, like mid-life crisis induced sports cars or shonky hair growth formulas. It’s for their good, as much as mine.
  • I do feel for the men who are “just looking for company whilst they travel” according to Clifford. Eating alone sucks. There’s only so long can stare at your phone while shoving spaghetti in your mouth and pretending you’re having a fun time. Eating with them is doing a good deed and getting paid for it.
  • I could re-enact every scene from Pretty Woman.
  • Accountability. I imagine this person will want to know what I’m spending their money on. Explaining to someone why I spent $200 on Amazon at 2am (inflatable pool toys, don’t ask) will be so uncomfortable, it will force me to stick to a budget.


  • If a rich guy is buying me designer shoes, he’ll probably expect me to wear them at dinner. As a novice high heel wearer, I will probably end up falling into Sydney Harbour while trying to act classy and adult when attending the opera.
  • Eating at fancy restaurants where they give you more than one fork and force you to work out which one to use and whether to keep it or let it be taken with your dirty plate at the end of the course. So much pressure.
  • The grimy feeling of being financially dependent on someone else.
  • Incredibly bad pub food is one of my guilty pleasures. If I’m ‘dating’ a rich guy, will I ever see the inside of a urine-stained, smoke-filled hole in the wall again?
  • Potential outlay. If I was going to do this properly, I would probably have to invest some time and money into it. No one’s going to take me to a fancy dinner in my tracky dacks. I might have to buy some better clothes and get my hair done in order to lure the rich men to my online dating profile.
  • Potential murder. Online dating in general makes me leery, because serial killers look just like the rest of us, and might even look like a genuine, friendly guy given the chance to craft an identity online. It’s even worse dating rich guys, because 1 in 5 CEOs are legit psychopaths.
  • Dating some guy I don’t know. What if he’s gross? What if he’s boring? What on earth will I have in common with a 50 year old banker? That we both like money I guess.
  • Accountability. Explaining to someone why I spent $200 on Amazon at 2am (inflatable pool toys, don’t ask) will be so uncomfortable. I’ll probably do it anyway.

The pros and cons come out even, which is frustrating. The solution? Sign up for a sugar daddy dating site and find out.

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