Sugar Baby Dating Disasters


Not that I’ve never said this before, but sugar baby dating can be pretty great. The money is anything from good to amazing, and will completely change your life in both the present and future. Every visit to the mall is like Christmas morning was as a kid, because you know any of those pretty things you see can be yours with a request.

WARNING – “Epic Fail” Sugar Dating Disasters Below!

There’s usually travel involved in sugaring, be it a little or a lot, which brings with it worldly knowledge and experience that you can’t put a price on at all. And damn it, most of the time it’s just FUN: the dates you go on, the lifestyle you’re exposed to, and the people you get to meet are all exciting and never get dull.

Sugaring is also delicate, though, and there are some rookie mistakes that can screw the whole thing up. One of the most fundamental of these is not treating it with the respect it deserves. Sugaring can and should be a lot more than this, but at the core, it’s a “job” in the sense that you can quite realistically make your living at it without doing anything else. And every responsible person I know takes their job seriously. That means you learn about it even while you’re doing it, you improve the skills that make you good at it, and you do the research that will make you better.


Dating Above Your Head

A friend of mine, whom we’ll call “Jenny”, didn’t get any of that. At 21, Jenny was sugar dating a 62 year old investment banker named “Thomas”. As you might expect from his job, Thomas was extremely connected with and interested in the exchange markets; they WERE his professional life, and he enjoyed following and talking about them in his leisure time. He made that pretty clear to Jenny; at least, I discerned as much from the fact that he bought her several books on the subject, got her a subscription to the Wall Street Journal, and encouraged her to read the financial news online every morning.

Learn how to become an online-only sugar baby here.

The thing is, from watching their relationship, I really got the feeling that Thomas’ motives weren’t entirely selfish; he had done very well working in finance, and I think he was trying to help set Jenny on a path that could have given her a bright future, too.

Sugaring disaster tales

Jenny, of course, was having none of it. She’s not exactly an “airhead”, but the things Thomas wanted her to learn and keep up on were too technical for her to find entertaining. What she didn’t understand was that it wasn’t about her entertainment; it was about doing her job well. Because she refused to learn about market trading no matter how much Thomas begged her, and because the subject was so important to him, they pretty much had nothing to talk about on their dates. They liked each other, they had fun together when they went out, and from what Jenny told me, their private time together was mutually enjoyable. But there was no conversation, because Jenny couldn’t keep up.

One night, after they’d been seeing each other for (I think) about a month, and Jenny couldn’t maintain a discussion about a recent stock market crash, Thomas became frustrated and snapped, “So I guess you’re planning to coast by on your looks all your life, huh?” Ok, total dick thing to say, and obviously that was their last date. But he’d given Jenny plenty of time to enter his world, and she just wouldn’t do it. Sorry, Jenny, but when you’re a sugar baby, reading up on what makes your daddy tick is part of the job.


Having Multiple Sugar Daddies on The Down-Low

Another common mistake, especially among those new to sugar baby dating, is to have multiple sugar daddies at one time. It’s pretty tempting: you’re making great money seeing a single sugar daddy, and he isn’t taking up anywhere near all of your time, so surely you could do even better by filling up your proverbial dance card.

The problem with doing this is that it gets dicey when feelings become involved, as they always, always do. Even so, I still believe this is extremely doable, when done between the right people and when everyone is completely honest with each other. So the real rookie mistake here is thinking you’re gonna fuck around behind your daddies’ backs like it’s all good.

Let me tell you about another friend of mine, “Lisa”, who thought this would be a good idea with her first sugar daddy, “Robert”, and her second (whom she picked up a few days after Robert), “Larry”. Because she feared it would be “awkward and stuff” (her words), she decided not to be honest with either Robert or Larry; that is, she didn’t tell Robert about Larry when the latter guy showed up, and she flat-out lied to Larry when she met him and told him she did not yet have a sugar daddy. Larry, at least, never weighed in on whether this would have bothered him, but Robert had been explicit that he expected sugar monogamy.

Having multiple sugar daddies can be a problem.

I’ll admit that for the first three or so weeks, things were going pretty well. Lisa went out on dates with both daddies on separate nights, always telling one that she was “busy” when she was seeing the other, and coming up with suitably convincing stories each time she needed to (though I think Robert was starting to get suspicious). Then Lisa shot herself in the foot.

Larry had just bought her a $700 Armani dinner dress that she’d been wanting for awhile, and she was ecstatic. At the height of her euphoria, Larry asked to have dinner with her again that Wednesday, even though she had said she was supposed to stay home and clean house for her mom that night. In reality, of course, she had promised to go out with Robert that night. Lisa was so drunk on the dress, however, that she was ready to give Larry anything he wanted. So her stupid ass not only agreed to see Larry on Wednesday, she even suggested they go to the same pricey restaurant (her favorite steakhouse) she’d been planning to dine at with Robert.

Then she hatched the “brilliant” plan of waiting until an hour before she was supposed to meet Robert, then texting him that her dog was throwing up non-stop and she needed to take him in to the emergency animal clinic. Robert understood and wished her dog well, and Lisa smugly went to dinner with Larry.

Things were going well until halfway through her filet, when Lisa got a text from Robert saying, “I see your dog is feeling better.” She looked around the room and spotted him sitting nearby with his wife, with whom he had decided to keep the reservation he’d made for himself and Lisa. Lisa had to finish dinner with occasional glares being strategically shot at her by Robert when his wife wasn’t looking. Now, what was her reason for not just telling Robert and Larry the truth from the beginning? Oh, right. It would’ve been too awkward.


Try Online-Only Sugar Baby Dating

When you steer clear of pitfalls like these, though, sugar baby dating can be pretty awesome. Maybe I’m just a goody-two-shoes, but I’ve found that when it comes to sugaring, honesty really is the best policy; it doesn’t always guarantee that things will work out in your favor, but really, it’s going to be even worse if you try to keep up webs of deceit.

One pretty easy way to avoid a lot of the stress that can normally come with sugaring is to just do it online. I’ve mentioned it before, but to briefly go over it again: you work on a camming site (Chaturbate is best for this, and in general) and attract whales, and some of them will be interested in becoming your online sugar daddy.

Get started on Chaturbate the right way here.

This is worlds easier than physical sugaring, not least because the daddies are usually more reserved in what they expect from you. It’s really a matter of maintaining a friendship (rarely is it sexual) with them over Skype and phone, and in exchange for that, you get a sugar daddy online who will often end up paying you just as well as a physical one. You do miss out on the nice dates and exotic vacations this way, but if you don’t want to risk the drama that sometimes occurs with seeing a daddy in person, online-only is definitely the way to go.