Never perform services for her, her family, her friends, etc. in your profession. If you’re an attorney, accountant, realtor, etc. it’s a no win situation. She’s never happy with the result. She expects you not to take a fee and, further, to pay all expenses yourself. Plus, these things take time normally, and, should the two of you stop seeing each other, now you’re stuck.
Also, I avoid any long term plans for travel. There’s always the risk that something happens in the interim that causes her not to want to go which can be very expensive.Akin to netnoys' and WK's recent posts about successes and failures, here are some absolute "never do's" I've had to learn about by "doing."
1. Never let an SB move in with you. An overnight or weekend is ok, but never allow her to move in, think she can move in, or get the impression you will consider letting her move in. At first glance, having her move in sounds ideal: essentially free, unlimited sex, no need for expensive hotel rooms, perhaps she will help with chores like dishes, laundry, bathroom cleaning, etc. But none of these will actually be realized. The sex will be less often, may still require payment of additional allowance, and will be less enthusiastic as she will now see it as an obligation. The chores and housekeeping will be left to you, and she will complain that you are a slob for not cleaning up, or you will realize that SHE is a slob who never cleans up. In addition, there will be NO other SB's! Certainly, no SB's can be invited to your (now shared) home, lest you face excessive drama (from the SB in your home who isn't fucking you anymore). But even trying to talk to a new SB, let alone book a hotel room and find an excuse to leave the home will be a pain in the ass. Finally, she will break or ruin stuff. Your expensive tech, your beautiful furniture, your car; all will suffer from her carless usage. In my case, she decided to take up oil painting in my living room, while drunk (which was daily). Within 30 days, there were oil-paint hand- and fingerprints all over the place.
2. Never sign, or co-sign a lease for anything, especially an apartment, or a car. But don't even co-sign for a phone bill or fuck's sake a bank account! You will be left with huge bills and ruined credit every time. Just stay away from all legal docs. Even if you already plan on paying the full bill every month, she can still expose you to problems by abusing the service. If you MUST take on one or more of her bills, then either giver her cash upon presentment of each bill, or make the contract fully under your name and you control access and use of the assets. I co-signed a lease for an SB in 2017 and I set up auto-payment for the 1st $1200 of her $1500 rent each month. At least 3 out of 6 months she would be late on her $300 portion, which meant I got the late notice and I had to pay to prevent my credit scores (which are north of 800) from suffering.
3. Never give her your credit/debit card or checking account info. This should be obvious. But it can happen without you noticing. I thought I was clever by opening a checking account at a bank I don't use. I put her name on the account and arranged for her weekly allowance (yes, monthly or weekly allowance will be "never do" number 4) to be direct deposited to that account so she could use the debit card on the account whenever she wanted to. But: The account was always over drawn, she lost the card 4 times, and my direct deposit ended up only funding the account penalty fees. This caused more than one heated discussion and I eventually had to shut down the direct deposits the same day I kicked her out of my home - lesson learned.
4. As mentioned, never agree to monthly or weekly allowance. Sure, it sounds more convenient. But it will cause problems:
- She will come to assume and then forget that she's getting her allowance and will then ask for more. Look, it's important to understand how an SB conceptualizes cash. Thirty seconds after you put those Benjis in her hand she has forgotten about them and is looking at you wondering when you will provide her next allowance. She's like a goldfish with a 30 second memory. Sure, she has $400 in her wallet from "somewhere," but that's HER money, and she needs Daddy to help with the next bill.
- The underlying assumptions for calculating monthly allowance will prove false. You may have agreed to say, $1200 a month assuming she will go BCD 1x a week with you forever. But life happens, she will miss one or more weeks for issues at work/family/travel/drama/etc., but will still want the full allowance and will NOT offer to (or agree to) "catch up" next week. Finally, at a convenient time of her choosing, she will claim that your monthly payments are made for the upcoming month, not the previous month and will demand you pay what amounts to double for the same month.
All of these, and I mean ALL, I have learned by "doing" the "never do's" and it has cost me dearly over the years.
I welcome any other input, feedback/pushback, or questions, because...
Life is good
The Cat
These hard-earned lessons from Herb are worth their weight in gold - the gold you will save by not making these same mistakes. Attractive girls can be very convincing and when the pussy is in your face, you are not going to be thinking critically. Never, ever have an SB move in with you!!!! This is Cardinal Rule #1! If you are looking for steady tail, you are far better off working at setting up regular arrangements that are PPM, NOT ALLOWANCE. You cannot and will not get value from an allowance situation for the reasons Herb mentioned. Yes, it's tempting. Resist the temptation and you will live to sugar again! Excellent post, Herb. 
As I just wrote on Netnoy's post, I've never encountered any of these issues. I've been lucky, or maybe smart enough to never go down the wrong paths very far in search of pussy! My worst idiotic mistakes have been to send $ in advance for promises that of course never materialized. So I have learned those lessons the hard way. And as I've always said, education is expensive! And another old saying is that stupid people repeat the same mistakes over and over, average people learn from their mistakes, but the superior person learns form the mistakes of others! May we all learn from each other's mistakes!
Herb, great post. Thank you for sharing these valuable lessons.
I'd like to add "don't catch feelings" as a never do. I acknowledge it's an abstract concept compared to the examples you described. That said, I feel it's often the driver behind SDs committing a "never do".
I will say, first off, I can afford to pay an entire lease. I can also afford to evict a shit SB if I want her out and use the place as a party pad. So, this leads into my first rule.
1. Know your budget and don't stretch it. She may say she's worth $10,000. But it's still one woman out of thousands.
2. Know what you want. Purely BCD? Dates in town with great sex? Daily communication? Be clear on it. If you have kinks. Tell her you do. Don't be afraid to say it's not a match.
3. If you are getting feelings, be very careful. She's usually a lot younger. It can be infatuation with a young girl, not real feelings. Give it far more time than you would think. Nothing wrong for caring for someone but don't let it go to your head.
We can never discuss this too much:
WORTH: It's NEVER about her "worth"! Ask literally any woman what she is "worth", and she will quickly tell you her worth is "priceless" or thousands or hundreds of thousands, or even millions of dollars. Even (or perhaps especially!) the fuglies will claim they are worth every penny you have plus a lot more. There is no concept of market value to a SB offering pussy for cash. Remember that an SB does not care if you need to take out a loan to date her. She just wants the money. And if that means you will end up broke and evicted, she's always ready to move on or spend more time and attention with any one of her other SD's (Always assume she is fucking other guys; SD's, a hubby or/and BF, and randos from a bar/class/church/party, etc.) Don't ever allow the conversation and allowance negotiations to wander into "worth" calculations. Just pull it back to...
BUDGET: It is ALWAYS about your budget! You must take time in advance calculating how much you can really spend on sugaring without missing the funds. If you are thinking about shorting your mortgage/rent, car payment, investment funds, childcare/alimony, or any other expense then you don't have enough cash to play in the Sugar Bowl, at least at the allowance level you are looking to pay. Remember that total Sugar cost is much more than allowance. There are fixed, ongoing costs like std tests, burner phones, etc. And there are per-BCD date costs like dinner, hotel, gas and/or airfare, shopping, gifts, tips, Ubers, and of course, allowance.
It may sound like geeked-out overkill, but I keep an extensive Sugar-budget spreadsheet on my personal laptop. It includes a disposable income (after tax) plan, my separate sugar-bank & credit card accounts info and balances, recurring costs as described, and straw-man date cost models for various types of dates like M&G's, BCD-Only, BCD "plus" dates, travel dates, gifts for birthdays, holidays, or special events (college graduation, or starting a new job, etc.). I don't make an allowance offer until I know what's expected for each typical date, and that includes things like BBFS requirements.
FEELINGS: This one is tricky. If you are not at least a little bit in love (and/or lust) with her, why are you there? But you are the adult in the room - that's why you are called Daddy! You must keep that love in perspective of the overall structure of a sugar relationship. It's important to review your SB from time to time, much like doing an annual employee performance review. Did she perform her assigned tasks, objectives and projects well (on time, high quality, within budget)? Did she have any behavior or policy issues (on time, happy attitude, handled "company" property correctly)? Should you consider a merit-increase? Do you have any positive feedback, or any constructive feedback on how she can improve performance or better adhere with policy? If you budget 15 minutes a month to "review" each SB in your rotation, you will be able to really understand what each one is "worth" to YOU (not her). Then you can decide on an action plan: retain, retain and promote with higher allowance, train or request performance improvement, or if needed, terminate the arrangement.
Sounds cold-hearted, right? Goddamn right it does. This is YOUR money, and your life. It's up to you to use the same level of critical thinking about business decisions in the Sugar Bowl as you make in your professional career decisions.
Life is good
The Cat
Your comment on feelings being tricky is spot-on. The emotinal connection is why I moved over to the sugaring world in the first place. Sessions with pro provider felt like driving through a toll booth and handing a stranger money. Even the better providers often felt like eating pancakes with no butter or syrup. The trick is to keep one's feelings from leading them into stupid decisions. And the way to do that is to always stay connected to your rational brain. Tricky, but necessary. Hearing other SD's cautionary tales can help a lot.
I agree with you 100%! The emotional connection that can sometimes happen in the sugar bowl is a big part of the attraction for me. The tricky part is knowing there's a line you must not cross, and figuring out where that line is and not crossing it, and refraining form allowing the emotions to lead you into bad decision making! I've crossed the line a few times and regretted it when she either ghosted me or talked me into making unreasonable purchases for her. I think I've learned my lessons by now. But this activity does have its emotional risks!
Never perform services for her, her family, her friends, etc. in your profession. If you’re an attorney, accountant, realtor, etc. it’s a no win situation. She’s never happy with the result. She expects you not to take a fee and, further, to pay all expenses yourself. Plus, these things take time normally, and, should the two of you stop seeing each other, now you’re stuck.
Also, I avoid any long term plans for travel. There’s always the risk that something happens in the interim that causes her not to want to go which can be very expensive.
I have taken two different SBs on a one-month trip that included a long-term cruise. In both cases, these were long-term (3+ years) arrangements, and I thought it would be all "smooth sailing" (an apt metaphor?) for the full 30 days. I was wrong, of course. Withing the 1st 5 days, problems started popping up. For one of them, I had to offer (threaten?) to put her on a plane (economy of course) back home the next day.
Considering that my all-in budget to take 2 people on a 30-day, multiple country trip (business class air, 5-star hotels, private wine tours, and a balcony cruise suite) was over $40k, I did not use my budget wisely! Now, my fault for it not working the 1st time. But sadly, also my fault for it not working the 2nd time, either.
So yes, beware of making large, mostly non-refundable or non-transferrable investments.
And as the old business saying goes about work and personal life: You don't shit where you eat. I always get a chuckle from POT's who suggest you hire them as a "personal assistant" at your company in their profile text.
[Begin Dr. Evil Quote] "Yeah....... right." [End Dr. Evil quote]
Life is good.
The Cat
Yeah, my biggest fuck up was hiring a long term SB I had serious feelings for. The one who stole from me. I needed someone to help manage a website. She used it to steal over $30,000 before I caught her. She's been arrested for it. This is the one that was married and cheating and living with a pimp.
This reminds me of a time that my employer sent me to a seminar on business management. It may not be directly applicable, but its a good lesson along the same lines.
One of the keynote speaker's primary points was: "If you choose to do work for friends or family (you have a choice), either; Do it for free. Or, charge full price." If you do it for free, and there's a problem, they have no reason to complain. If you charge full price, and there's a problem, you don't mind dealing with complaints so much.