How To Date Multiple Sugar Daddies…and Why You Should

By Caitlin

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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. Juggling multiple sugar daddies is something you will most likely end up doing at some point as it’s rare you’ll find your perfect sugar daddy early on.

I would actually advise you to keep your options open as it is almost certain any man you are speaking to is doing the same. However, while most (if not all) of the men you’ll speak to are happy to date more than one woman at the same time, they tend to disagree with you doing the same (double standards, I know!).

If you do eventually meet the ideal sugar daddy for you (congrats to you!!), then by all means, end any other arrangements you have but until that point, you will need to learn how to handle more than one at a time. Here’s 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. 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 isn’t enough hours in the day. 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 and if you’re distracted by so many SD’s 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 SD 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 SD 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 men 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!

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(1) comment

Fox May 21, 2019

“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.

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