Okay, you’re not sure about asking a SD for money because you keep seeing advice against telling him about your financial troubles. I will be one of the first to admit that asking a SD for money is not easy at all. You have to remember that when you ask for nothing, that is exactly what you will get. I learned that lesson the hard way. There is a difference between discussing your needs, expectations, etc. and complain about your bills. Everything is in focus.
With the men you meet through a Sugar Daddy dating site, it’s a matter of who takes charge first. Don’t wait to talk about what you expect of them. They signed up knowing exactly what kind of website they were on. Your expectations should be a topic that is discussed very early in your relationship. If you have a short first meeting and there is no time to bring it up, then (and you it should mention it), talk to him before your second meeting. If you don’t, you have lost control. All you have to say to start the conversation is, “We need to talk about what each of us expects from this.” You don’t have to ask for much. If you see it 3-4 times a month, $ 200 each time they meet is a reasonable place to start. For an out-of-town sugar daddy you see once a month, aim for $ 400-500. In any case, you can increase your contributions little by little.
Now, if the man in question is someone you put “on the street,” he might not even know he’s a daddy. This approach can be a bit sneaky, but try to get something out of it every time you see it. At first, you may want to “go out with your friends.” Next time, maybe your “car needs some repair.” Make sure you’re not a genius mechanic if you choose that one (unless your car really needs work and you don’t mind me doing it). He will come to anticipate your needs and will begin to give you money freely on a regular basis.
With either type of sugar daddy, you can work to pay your car, rent, or mortgage payment. You can also convince him to pay you to go back to school or to help you start a business. The key is to overcome doubts about letting him know what he needs. Very few of the sugar daddies I’ve ever met were shy when it came to what THEY wanted.
Suppose you’ve been seeing a daddy regularly shower you with gifts, but what you really need is money to pay your bills. After you’ve been seeing a sugar daddy for a while, it will be more difficult to broach the subject than with someone new. In any case, you still need to test the waters. Sit down with him and have a frank but friendly conversation. You may want to start off by saying, “I really enjoy spending time with you. I love that you buy me x, y, z. But I really could use a little help with my rent / mortgage / car payment.” Judge your reaction to that request and choose your next move.
If you freak out, or are more interested in having a girlfriend than a sugar baby, or feel like you would buy your “services” if you give them cash. You may be able to wear it out over time, but don’t count on it. I’m not suggesting you end the relationship, but keep looking and meeting other potential sugar daddies. Eventually, you will find a man who doesn’t panic when you bring up the subject of an allowance. Instead, they will be more than happy to help you.