How It Really Is To Date A Sugar Daddy

How it started

It all started with a swanky restaurant, me in my best dress attempting a “I belong here” chic look, and him, slightly older (ok 10 years older, but age is only a number), well spoken and well dressed.

And very cultured — that is how he got me. He could speak about arts for hours. He liked opera (or at least he went to a couple) — and I was sold. I had not met many that ticked these boxes.

While he seemed successful and mentioned some projects he did not seem overly obsessed with his work — which was, for me a welcome change after a workaholic ex.

Turns out, over the course of our date he is a trust fund baby. And he works for fun essentially.

I put two and two together and it turns out I actually know his family.. well I know of, as they were clients of the private banking division of my former employer — which somewhat reassures me, otherwise I would have gotten some serious Tinder Swingler vibes. Was the protagonist supposed to be from a family in the diamond business or something similar?

But I must admit, a “nepo baby” is not my type. I do appreciate that at least is trying to do something and working even if he doesn’t have to. If I had a trust fund I feel I would go completely crazy on projects, foundations.. you name it. You literally have the funding to give life to your ideas, instead of having to work on them alongside a soul crushing job that you need to pay your bills.

So back to my date, flashy — i am talking designer clothes and a watch that is worth more than my brother’s car (I wish I could say my car, but I am an awful driver and I can’t drive).

So he invited me to a high-end restaurant. And not just high-end, the kind of in your face fancy restaurant.

I am already a bit sweating but when he organized he made clear “my treat, it goes without saying”.

Great, as I need to buy a new laptop and that is essentially what the bill would come up to for the night.

Why Aren’t We Kissing?

He was very galant.. and flirty obviously.

And we see each other another few times. We don’t kiss.. although he hugs me and he is definitely touchy feeling. To the point I wonder why we don’t kiss.

I later realize he wanted to be sure I was ok with the agreement first. And looking back I can’t help feeling a bit grateful for his sort of intellectual honesty.

As we sip expensive wine I don’t particularly like he finally lays out his life philosophy — all between humble brags about his exotic vacations and busy unconventional lifestyle, he slips in the real kicker: he is on the hunt for a sugar baby, not a girlfriend.

So it turns out I went out on a date with a sugar daddy. Well, more than one date really.

Then he mentioned a $10,000 monthly stipend. And I put 2+2 together and I realized he was a sugar daddy.

How did I miss the signs? Well, that is pretty typical of me really.

That was a cold shower.

I mean I was not 100% sold on the guy as a potential husband. But — I enjoyed being pampered and I thought we had nice conversations.

I then felt he was basically just showing me what he could offer on his side of the bargain. I mean, no wonder all the locations were so extravagant and he insisted on paying everything.

And he casually mentions a $10,000 monthly “stipend” for expenses, beauty treatment and what not.

So he is on the hunt for a sugar baby that understands the importance of non-exclusivity, not girlfriend style nagging about not spending enough time together.. and appreciates a good stipend for a “low maintenance” arrangement.

You know, nothing says romance like a semi-contractual allowance.

I wish someone taped my facial expression.

How did I graciously get out of the situation?

I laughed it off, as per usual — although it was undeniable awkward. especially as he continued jokingly say to give it a try and make up my mind after a weekend away somewhere.

By dessert (which, by the way, was a delicious creme brulee), I could not wait to leave.

A monthly stipend was not an outrageously bad offer to tolerate someone’s company and I admit it could sound tempting in a world filled with rent and increasing cost of living, I’m afraid I would not enjoy being someone’s arm candy and too opinionated (as he was looking for someone “submissive” in his own words).

I mean, who has time to listen to someone’s monologue about their “hard life” as a trust fund baby when there are books to read, shows to binge and worse comes worse, real bad dates to go to?

Despite my “Thank you but no thank you”.. no judgment here.

I get that for some can work — after some research in my forums about the sugar daddy sugar baby lifestyle (the date did spark my natural curiosity), I came to know there are apps like “Seeking” are out there facilitating these connections.

Which made me think, if there are these options out there.. why would you use regular app and risking losing people’s time (as in my case)?

This sparked a little research and I contacted a few people with experience on such “arrangements”.

And while all experiences and cases are unique, some elements were surprisingly recurring (and made me glad I did not pursue that for myself as I don’t think it would have been a good match for me).

The sugar daddy was older, sometimes significantly

Based on the cases I have seen or spoke to, anywhere between 10–30 years older.

It was always non exclusive – from the sugar daddy side

I have read it is not always the case, but the girls I spoke to told me it was pretty clear from the outset that the sugar daddy could be free to do what he wanted (and was sometimes married).

It was often, but not always, exclusive from the sugar baby side

While the sugar daddy was for all intents and purposes single, the sugar baby was often expected not to engage in other relationships (being it other agreements or dating). This was not always the case, and one girl told me her sugar daddy is significantly older (and married), is happy to enjoy her company on some trips but there is a mutual understanding she is dating and looking for something serious in the meantime (I must say, I imagine it is not easy to bring it up on a date.. “oh btw I hope you don’t mind, I have a sugar daddy”)

You don’t always get a check/stipend

Unlike my date, not all sugar daddies give outright stipends to their sugar babies. Often it is more in the form of gifting or refund for expenses. The sugar daddy would be happy to pay for fancy haircuts and treatment, beauty treatments, clothes, bags etc.

You can catch feelings more easily than you think

This is something I can very well understand. I also think it is one of the main reasons while I feel it would be quite dangerous for me to get in such an arrangement.

You get someone that showers you with attentions and takes care of you. You feel pampered and all and it many cases it becomes your safety net financially. It is possible you start to attach romantic feelings to the situation. And you start to want more.

Now this happens and it does not often end well as by construct the men entering this agreement don’t want to offer anything more, and certainly not commitment (and in certain cases they are married or in a relationship/family).

Spending time speaking with people that have various points in their life engaged in these agreements just reinforce my belief it would have ended up very poorly for me so I am somewhat relieved I said no, yet the questions stands..

Why didn’t he tell mefrom the outset?!