How To Date Multiple Sugar Daddies…and Why You Should

By Caitlin


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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