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How to Begin & Keep The Best Sugar Daddy Relationship You'll Ever Have

girl with beautiful diamonds
Expensive gifts are a perk of sugar daddies

I had a friend in university — we’ll call her Anna — who revealed to me one day that she was flat out broke, with almost no money for rent. I offered to help her out, thinking she would pay me back but she announced to me she had quit her job.

I was mystified. Anna didn't seem at all perturbed about her financial status. I remember asking her how she would manage and she told me then, with an impish grin, that she had an ace in the hole. I learned, several months later that her “ace in the hole” was an older gentleman — quite a bit older — who was responsible not only for paying Anna’s rent but was also the reason she was sporting this expensive new jewelry.

I was intrigued. I wondered if sugar daddy dating was for me. After all, what woman doesn’t dream of being completely pampered and lavished with gifts all the time? Just for being herself! I approached Anna with my questions, and she was only too happy to oblige. Anna mentioned that there were classic mistakes everyone made when it came to sugar daddy-sugar baby relationships. She told me that if I wanted to be successful from the start, there were unspoken rules to the game that I’d have to abide by.

Far from deterring me, this actually made me even more excited and eager. Once I avoided these mistakes, my dating life changed forever:

1. What’s Your Sugar Baby Flavour?

When you get online, the first thing you need to figure out is what persona your sugar baby embodies. Is she bold and sleek? Is she the femme fatale? Is she polite and well-spoken? Is she wild and spontaneous? Don’t mistake any of this to mean that you need to be loud, obnoxious, overstated and aggressive. Sugar daddies like women who portray their fantasies, not overtake them. This is a very delicate and yet important thing to understand when it comes to sugar dating. So get your alter ego down right. You can even give her a cool backstory. Think of this as your chance to really let go and express yourself.

2. Embrace the unconventional

Sugar babies live a very unconventional lifestyle. And if they’re good at what they do and strategic about who they date, they can also live a very lavish lifestyle. Being unconventional is par for the course. It becomes messy when you mix up social norms, expectations and personal culture in the mix so keep it as compartmentalized as possible.

Don’t think too much about what others are doing — be confident in your own path. This is why having an alter persona, someone whose shoes you can step in to, really works. This woman that you’re becoming is not necessarily the entirety of who you are — only a part of you. So while she’s around, take full advantage of the unconventional lifestyle she lives and the perks you get to enjoy, thanks to her. Once you lean in to the unconventionality of dating someone way older but with way more money, you’ll really be able to embrace it.

3. Sex Is Always On The Table — But Never Guaranteed

Sugar babies are one half of a consenting and mutually beneficial relationship when it comes to sugar daddy dating. One of the allures of maintaining a sugar daddy-baby relationship is the financial perks for the sugar baby and the sense of being able to be with a younger woman, sexually, for the man. But many sugar babies report that they get a lot of pleasure from their connection, whether sexual or intimate.

Sugar daddies don’t always expect a date or an encounter to end in sex and you, as a sugar baby, should not set that standard or highlight that expectation. It keeps the mystery alive, not knowing when the next time is going to be, sure, but there’s many more practical reasons why sugar babies should not guarantee sex. Sometimes, sugar daddies date younger women to mentor and guide them. They may love the companionship, the lightness of experience and the personality of their babies.

So while sex certainly enhances these connections, not keeping it as a given means that it feels more organic and authentic to both parties. So even though money may be changing hands or a bill may be covered here and there, the emotional connection actually enhances this relationship.

man drinking champagne with two girls
It is not just gifts - it is a relationship

4. Let’s Haggle

On the flipside, it’s important to be totally clear and precise on certain aspects to the relationship. Here is where it gets a little different — and maybe even a little trickier — with sugar daddy dating than it does with regular dating.

While both parties agree that it’s a fabulously mutually beneficial arrangement, both parties also have to be clear on what those arrangements are. The truth of it is that both sugar baby and sugar daddy are well-advised to keep their guard up because, besides emotions, there’s a lot more at stake, such as time and money.

Decide at first on the particulars: how many times a week do you want to see each other? What kind of maintenance does your sugar daddy (and sugar baby!) expect? Where will you won’t (and what’s off limits?) How long are you looking for it to last and what are your (and his) deal breakers?

5. Billable Hours?

Look, the point is that screening through eligible men as a young and beautiful single woman looking for a sugar daddy relationship is going to be time-consuming. Do the work and approach your search exactly like work. No, it doesn’t have to be tedious but, yes, you do have to be thorough in your search. And don’t be sharing selfies to men who haven’t earned them.

Just like sending out your resume, browse through profiles and meet with prospective sugar daddies to find the right one (or more than one!) And don’t be afraid to cut out prospective babies (or daddies) if the arrangement doesn’t suit you or if there are red flags you’re not immediately okay with.

6. Be Clear On Your Whys — & Share ‘Em

There’s a particular reason why sugar babies choose to be sugar babies. Some want to upkeep their expensive habits and tastes, others want to trade up and have extra cash on the side to pay off loans and others simply don’t have the time to pursue long term dating since they’re busy focusing on building a career and figure this is a great way to have a relationship and some extra benefits. And some women just want the wild lifestyle and experiences with older, financially stable men.

No matter what you’re particular reasons, be absolutely crystal clear on them — this goes for sugar daddies as well. You should know why your sugar baby is dating you — what she’s looking for, what her expectations are — and how you can help her with her needs. More than simply being benign, having this honest conversation is necessary so both of you can know what’s on the table and when it’s time — if ever — to “cut cords”.

rich man with a drink and two girls in his hands
A sugar daddy should always be a perfect gentleman

7. Keep It Classy & Drama Free

And, finally, be a smooth operator. At the end of the day, even though your sugar daddy loves the feel of younger women being attracted to him, he wants a woman who has a handle on her life. If he’s a lot older and financially successful, he wants a woman who can be the perfect companion, a complement on his arm, not a time-bomb waiting to go off.

Practice the art of sharing — without oversharing. Being a sob-story all the time, sharing your daily and mundane life woes with him is only going to kill the genuine romance that may be budding between the two of you. And sugar daddies should never accept or receive sloppy behaviour from their sugar babies, just as sugar babies should never accept their sugar daddies as anything less than perfect gentleman.

The point is to be clear and as brutally honest as possible. Then, cash in on the perks you’re looking for while still enjoying the relationship you’ve always wanted.

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Image sourcesImage 1 - NeonshotImage 2 - KzenonImage 3 - Kapsers Grinvalds