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How To Date Multiple Sugar Daddies…and Why You Should

At first glance, dating multiple sugar daddies sounds like a shortcut to a very abundant lifestyle.

You think: if I’m getting a sugar baby allowance of $xxxx from Sugar Daddy A and a PPM of $xxx from Sugar Daddy B and my rent and bills paid from Sugar Daddy C…I’ll be wealthy in a few short years.

But the reality rarely works out that way. Which is why it is the rare sugar baby who can successfully date multiple sugar daddies – especially for the long term.

Here’s a deep dive into the reality of having multiple sugar daddies. After reading the pros and cons, you’ll hopefully have a better idea whether this lifestyle is for you.

Can You Have Multiple Sugar Daddies?

Yes. In fact, many sugar babies date multiple sugar daddies – especially in the beginning of the sugar daddy search. It’s similar to “vanilla” dating where you casually date a couple people to see you connect best with. So juggling multiple sugar daddies is something you will most likely end up doing as it’s rare you’ll find your perfect sugar daddy early on.

And in the beginning, I would actually advise you to keep your options open as it is almost certain any potential sugar daddy you are speaking to is doing the same.

The thing is, though, most sugar babies aren’t doing this as a long-term strategy. They’re simply playing the field and testing the waters until they find the sugar daddy of their dreams.

But what about after you find a great sugar daddy and enter into an arrangement? Can you have multiple sugar daddies then? Well, it depends on you.

Depending on who you are, dating multiple sugar daddies can sound like a really grand plan. Or just a whole lot of unnecessary complication.

To see which side you fall on, let’s go over the pros and cons first.

The Pros of Having Multiple Sugar Daddies

One sugar daddy is good. Multiple sugar daddies are great. Right? Well, yes. Here are the main perks of dating multiple sugar daddies.

  • Sugar, sugar, and more sugar. Sugar daddies offer various forms of sugar – there’s the sugar baby allowance, rent and bills paid, PPM, tuition assistance, and then there are the luxuries like gifts, lavish vacations, posh restaurants, and experience you’ve only dreamed of. Having multiple sugar daddies gives you access to the full spectrum of sugar available.
  • You’ll learn a lot. Even one smart, successful sugar daddy can change your career trajectory and life path. Not imagine you had multiple sugar daddies – all with their own life wisdom, career connections, and business insights. Oh, the places you will go.
  • You can choose sugar daddies you get on best with. There are times when you’ll meet a great sugar daddy who is cute, kind, and you just get on with…but he can’t afford your allowance. Having multiple sugar daddies can allow you to be his sugar baby because you’re getting your financial needs met by other sugar daddies as well.
  • There are no “broke” periods. If you’ve been a sugar baby for any amount of time, you’ve encountered your fair share of flakes and Poof Daddies. When you have multiple sugar daddies, however, when one goes belly up – you have several others to fill in the gap.
  • You’ll never get bored. Some sugar babies like the constant flurry of activity, the interaction, and yes, the intimacy, that having multiple sugar daddies provide. Especially since sugar daddies tend to be very busy men who don’t always have time for you.

And these are all very good reasons to have multiple sugar daddies. But there are downside, too…

The Cons of Having Multiple Sugar Daddies

If there weren’t very real downsides to having multiple sugar daddies, most sugar babies would choose this route. But the reality is, these drawbacks can be enough to put most sugar babes right off.

  • You don’t get a break. This one is obvious. If you are juggling multiple sugar daddies, you are going to be very, very busy. Even one sugar date a week can be a lot. But imagine going on two, three, even five sugar dates every week. It can get tiring fast.
  • It can be emotionally draining. It’s not just physical exhaustion, either. Most sugar daddies aren’t just looking for pretty arm candy to sit there and nod. They want banter, emotional connection, inside jokes, to feel listened to and cared for, and for you to remember that they hate onions, but love scallions. Being a carefree escape for multiple men can result in serious burnout.
  • Little time for your own life. Unless your only goal is to make as much sugar as possible, you probably have other life commitments, i.e. school, work, and even just hanging out with friends and family. Dating multiple sugar daddies will take up the bulk of your time and energy, which means there’s little leftover for your own life.
  • Higher risk. If you’re going to be sexually active with multiple sugar daddies, that comes with an increased risk of STDs and even pregnancy. So you’ll have to be extra careful on this front.
  • You may need to lie. While many sugar daddies (if not all) you’ll date are happy to date more than one sugar baby at the same time, they tend to disagree with you doing the same (double standards, I know!).

How to Date Multiple Sugar Daddies

Multiple sugar daddies come with a range of perks as well as some very real drawbacks. But if you can handle the downsides or if you want to play the field until you’ve landed the perfect sugar daddy, here are 3 tips on how to date multiple sugar daddies at once!

The one you’re with gets your full attention

Whether they are the only sugar daddy you’re seeing or not, they have to feel like they’re a priority to you when you’re speaking to them or when you’re spending time together.

This is crucial. You need to be fully present with the sugar daddy you’re spending time with.

Whenever you are texting or on the phone, give them your full attention. Don’t be watching TV or scrolling through Instagram as you talk.

Be engaged in the conversation – if he tells you on the phone that he is heading off to a baseball game with his buddies next week, be sure to ask him how it was next time you meet. It will make him feel appreciated and think about if it was reversed – you’d appreciate him paying attention to you and it works both ways!

Keep your appointments

You should also try your best not to cancel dates – once is OK, twice just annoys people. You don’t want to be involved with so many men that there literally aren’t enough hours in the day.

Although I have had a couple of arrangements and relationships that were exclusive, most of the time, particularly when I was living in New York, I was dating a couple of men at once.

The most men I’ve been seeing at one time was three.

Two I met weekly and one I would fly to meet in Texas once a month. You don’t want to be confusing people with one another or forgetting things they have told you. Again, imagine it was reversed and he was mixing you up with someone else – I know I wouldn’t be happy!

I always gave them my full attention when we were together. If you’re distracted by so many sugar daddies that you don’t do this, there’ll be someone else who will.

I’d also advise you to invest in a day planner. You can obviously write down any dates you have with people but I’ve also found it handy to write down little details about them as well.

For example, when I would fly to Texas each month, my sugar daddy had usually been to at least two states since the last time we spoke, as he travelled a lot for his work. I always made a point of writing down where his next couple of meetings were whenever he told me so that I could ask him the next time we met.

Honesty really is the best policy

While I don’t necessarily advise you to be completely open and tell your sugar daddy that you are seeing multiple men, I’d also advise you to be honest if you’re asked about it.

Exclusivity can be a big deal to some sugar daddies and if he would prefer you to be seeing him and him alone, try letting him know what your needs are and if he is willing to match them, you’re happy to be exclusive.

This can be tricky as he might not be able to match them and he might either want you to end your arrangement with the other man or even worse, they might end theirs with you but I’ve found in the past that it’s even worse to be caught in a lie.

A simple solution is just to keep him happy. He’ll only realize if you cancel multiple dates or get him mixed up with somebody else. All the more reason to follow the tips above!

While you might feel guilty for seeing more than one man at the same time, I would actually recommend doing so. It allows you to really see what’s out there and more importantly, it’ll show you what you want from a sugar daddy.

It’s not rare for these men to be dating more than one girl at once and if for whatever reason, they end things with you suddenly, you won’t be left single (and broke)!

This post is brought to you by one of our contributing SB writers, Aly, aka The Travelholic Sugar Babe. You can check out her sugar baby story here!

2 thoughts on “How To Date Multiple Sugar Daddies…and Why You Should”

  1. “A simple solution is just to keep him happy.”
    Yes. That’s very good advice. Choose well, keep them happy.

    ” He’ll only realize if you cancel multiple dates or get him mixed up with somebody else. ” On no. NOT good.

    Do you ever recall hearing anything about dating men older than yourself which mentions the things you can learn from their Life experiences? Also, do you remember ever hearing of the expression about a “Woman’s Intuition” ability? A person with experience can seem to “feel things” as if from the Ether. You amaze children and pets for a magnified but similar reason. Knowledge.

    The more life experience with people, and one starts to read them, like having extra intuitive ability. Facial cues, word/phrase/nickname choices used, tone of voice, as well as minutia that either adds up to what one expects to see, in that pattern of accepted Reality, or something does NOT line up properly.

    Then, even if not consciously, there is doubt. “You don’t add up now, for some reason.” Tons of people in any situation seeing another, are noted as having someone else EXACTLY like that. Then pull the string. It unravels them.

    The kitten. Cute, right? But toying with adults needs to be way limited. Pull it away a little, then reward, or you are one of the sugar babies that looks like just a tease, whatever you must be getting from it. Like “catfishing” people. Treat guys that are “The John” this way, since they want to treat you like a toy as well.

    The kind of Sugar Daddy you mostly will want, will be financially stable and will think of you as a Person who interests them. Treat him as a respected equal, and you may find he prefers treating you the same, or that he already was treating you that way. Disrespect, even perceived, turns women and men off.

    Being intellectually insulted is my least favorite kind.

    I’m working on one, ONE, “sugar business baby”, let’s call her. Is it because I’m too lazy to look around more? No. Women approach me. I could have a few women I see and am not supposed to care about, just organically as I go through Life. She’s particularly special.

    She’s a beautiful 26 year-old who likes to say “25”. She’s funny and talkative. She has enough intelligence to practice Law, and do it well, so plenty.

    I’m laying out my proposal, including paying for her coming graduate school. I look forward to likely romantic dating, taking her to festivals and shows, overseas travel when I can tear her away from her schedule, and who knows what kind of awesome it can be.

    She benefits, I benefit, and we both count as people the whole time.

    If I am played with, it will be all over everything she says, and there will be 80K less coming her way. This woman would be a WAY quality companion, but not if she starts playing Junior High school games and becomes a little girl, right in front of me.

    Remember your exes? Men remember theirs too. You are part of the solution , so creating new problems is like the zipper that won’t zip.

  2. Unless the woman is a complete emotionless sociopath, a SD will know – given that he doesn’t willfully ignore it. Best option is just get one that is so busy that he doesn’t care. If the SD cares, he will know. Its like a suburban white guy trying to talk like he is from the hood – the act will never be genuine.


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