Testing His Generosity, or Just a Hustle? Why Asking for Gifts Before the First Date Never Works
Hi, everyone. I’m Tim Parker, your resident unreliable writer, back to share a few more completely unprofessional thoughts on the dating world. Haha.
Today, I want to tackle a topic that comes up all the time: women asking for gifts or small cash transfers before ever meeting in person.
A Hustle Known Across the World
Yesterday, I stumbled across a fascinating news story. What caught my attention was that it didn't happen in New York or London—it happened in China.
An eighteen-year-old girl openly broke down her full-time "career" over the past four or five years. Her entire routine revolves around sweet-talking older men into sending her money—a tactic colloquially known over there as "milking old guys."
She brings in an average of about $1,200 to $1,500 a month, with major spikes on Valentine’s Day and unofficial romance holidays, pulling in hundreds or even thousands in twenty-four hours. She has accumulated over $30,000 in savings, almost entirely through this playbook.
Her setup is methodical: she maintains a steady roster of more than a dozen men who regularly send money, reserves one full day every week purely for scouting new targets, and casually refers to all of them as "the bosses."
Her motto? "Anyone who hands you cash is a boss."
The Familiar Playbook: Sugar Babies vs. Sugar Daddies
Reading that story made me smile, because the parallel was impossible to ignore. The routine this girl ran mirrors almost step-for-step what certain self-proclaimed "sugar babies" pull on prospective "sugar daddies."
Even better, if you spend five minutes browsing dating forums, Reddit threads, or TikTok comments, you’ll see an endless stream of sugar babies venting about and criticizing sugar daddies with the exact same talking points:
- "I don't think asking for an upfront gift to make sure a sugar daddy is serious is a scam. If they can get away with paying nothing, they will."
- "There are so many pretenders out there playing sugar daddy, but the second money comes up, they start shaming the sugar baby."
- "Asking for a small transfer or gift before meeting is just testing whether he has real money and genuine intentions."
- "As a sugar baby, I need that financial guarantee just to feel safe."
- "I’m just asking him to cover my Uber. If he can’t even do that, why call himself a sugar daddy?"
Putting that news story next to these community complaints, do you really think it’s just a coincidence?
The script is identical: from extracting cash out of older men halfway across the globe to the daily critiques of sugar daddies on Western forums, it’s the exact same play under a different name.
Generosity Can’t Be Extorted
Here is my completely unprofessional take. I stand firmly with the vast majority of experienced men on this: when a woman is aggressively pressing for cash or gifts before you’ve even shared a handshake, odds are very high she is either running a hustle or has zero genuine interest in meeting you.
I know saying this out loud might ruffle some feathers among attractive ladies. But speaking man-to-man, this has nothing to do with whether someone can afford it, or whether he is generous.
It simply kills any interest in taking the conversation further.
Look at it from a basic human standpoint: nobody enjoys feeling like they're being shaken down or morally pressured into paying an entry fee for a cup of coffee. High-achieving, established men didn’t get where they are by being naive, and they certainly don't like being manipulated or treated like a mark.
When a successful man treats someone well or showers his partner with gifts, it comes from his own desire—driven by genuine chemistry, mutual attraction, and good vibes. Not because someone cornered him into proving himself with an advance deposit.
Where Safety and Fairness Actually Belong
To be fair, I completely understand the hesitation on the other side. Nobody wants to waste their evening on time-wasters, fakes looking for a free ride, or situations that feel unsafe. Every woman stepping into this scene hopes to meet someone genuinely generous and attentive.
However, leading right out of the gate with demands for cash guarantees is guaranteed to alienate the very men you actually want to attract. It sets a transactional, defensive tone before things even begin.
In my view, creating a safe, level playing field isn’t something users should settle through awkward pre-date negotiations. That responsibility belongs to the platform itself. Let the service establish clear rules, verify profiles, and filter out bad actors.
The members should just be able to sign up, connect, enjoy genuine conversation, and meet up like two real adults.
These are just the personal musings of one very unprofessional writer. Take them for what they’re worth—not as formal advice.