I’ve been a sugar daddy for 20 plus years – here is what I’ve learned

  • A sugar daddy has fielded questions on Reddit as part of an Ask Me Anything
  • The man, who lives in LA, gained his fortune from a 1990s internet startup
  • Now 53 years old, he explained he took on his first sugar baby at age 30

A man who claims he’s been a sugar daddy for more than two decades has opened up about his experiences and insights.

The self-proclaimed sugar daddy, who goes by u/Southern-Air5484 on Reddit, declared in a post: ‘I have been a sugar daddy for over 20 years with multiple women AMA (Ask Me Anything).’

Countless users poured into the responses to ask him questions, leaving upwards of than 1,300 comments across various threads.

Across his responses, a portrait of the Sugar Daddy, whoever he is, gradually emerged.

A 53-year-old man claiming he'd been a sugar daddy for more than two decades has opened up about his experiences and insights in an 'Ask Me Anything' session on Reddit (stock image)

The man is 53 years old, lives in Los Angeles, holds a PhD in history, and encountered his first sugar baby at age 30. 

He’d previously hit it big after getting involved with an internet start-up in the 1990s – and the financial windfall from his share of the company was sizable enough that, properly invested, he’s barely had to work over the decades.

Asked what his net worth is, the original poster (OP) reported: ‘I live on the beach in the Malibu, so yes, I am wealthy, but I am not a billionaire or anything.’ 

On where his wealth originated, he elaborated: ‘I was lucky enough to be part of an internet start up that blew up when we went public back in the 90s. 

‘Never in a million years did I expect to be in this position. I was actually in grad school to be a history professor and life threw me a curve ball and I was luck enough to hit it.’ 

Coincidentally, his introduction to the world of early tech companies dovetailed with his introduction to the world of sugar babies, as he wrote in another anecdote.

‘I literally got a job with an internet start up because I was nosy about finding out what a table full of nerds with laptops out and one older guy with an extremely hot girlfriend were doing in a coffee shop as I was working on my thesis,’ he recalled. 

‘I sort of butted into the conversation after overhearing what they were discussing and becoming very interested, and before I finished my coffee I had a job offer. I worked for a little above minimum wage and stock (which were so worthless we called them toilet paper) in the company while finishing my MA and PhD.’

Through his responses, the sugar daddy painted a broader portrait of his own background and his relationships to his sugar babies

He then described that he had ‘a little money from a trust fund my Dad set up before he died,’ and took that to buy stock from his coworkers ‘because they needed money, and I was betting we would take off.’

‘When we went public the toilet paper went from s#!t to golden overnight,’ he said.

‘I worked very hard while I was there, at least 80 hours a week plus grad school, but I will be the first to admit I was extremely lucky. I was born at the right time to be a computer geek when the net was being born, and was nosy enough to want to know what a model was doing at a table full of guys who made Bill Gates look like George Clooney.’

He also gave the run-down on how he’s found his sugar babies in the past.

Of the sugar baby-sugar daddy matching website Seeking, he advised against going on it, writing: ‘Once upon a time it was a wonderful resource, but it is pretty much filled with scammers and escorts at this point.’

He went on to suggest that if someone was ‘not in a large urban area with many available men, then maybe Tinder is a better option as it has worked well for me.’

‘Just use a phrase like “love to be spoiled” or another hint like that in your profile,’ he added.

‘I live in LA, and there are bars and clubs that are well known for the sugar scene. The Polo Lounge in the Beverly Hills Hotel for example is filled with models and actresses looking for a Daddy, but that takes a lot of self confidence on your part to just walk in and conquer the room.

‘But I have had luck in the strangest of places. The cute barista who I always flirted with. The cashier at my local supermarket. Just a beautiful girl whose eyes met mine and I struck up a conversation with.’

The sugar daddy also explained what benefits each sugar baby got out of the ‘arrangement.’

While it ‘varies a great deal,’ he said that on the ‘high end,’ with girls who have lived with him, he’s paid for their college and ‘provided enough that they built a nest egg for their future.’

He further wrote that he had three ‘long-term arrangements’ and  ‘all three are still very good friends.’

Elaborating on his ‘type,’ he wrote: ‘Beautiful, smart, strong willed, just crazy enough to put up with me, and someone where a long silence feels like joy shared.’

Of whether he’s remained platonic with any of his sugar babies, he explained: ‘I am really looking for an arrangement that is close to girlfriend I take care of [rather] than sugarbaby/sugardaddy, so yes, sex is definitely part of it.’

Elsewhere, he added of his preference for the degree of intimacy in the relationship: ‘I am looking and always have looked for something long term and with true friendship and intimacy. Given that I am still friends even years later with everyone I have gone long term with, it has worked for me.’

The sugar daddy also emphasized of his personal taste in sugar babies: ‘Looks might get someone in the door, but smart, funny, nice and talented is the only way the door remains open. And let’s be honest, if you have those, then beauty truly comes from inside.’

In turn, answering a question about how one might become a sugar baby, the sugar daddy stressed: ‘If you see an older man (40+ at least) who seems to be well off, just strike up a conversation and see how it goes. Only an idiot thinks a hot young girl is flirting with him when he is twice her age and not expecting something in return.

‘Just have the confidence to look in the mirror and say I deserve the lifestyle I desire, not out of arrogance, but out of a sense of self worth.

‘And when you find that Daddy you seek, never let him disrespect you, no matter how much he is giving you.’


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