Okay, so you’re not sure about asking an SD for money because you keep seeing advice against telling them about your financial problems. I’ll be one of the first to admit that asking an SD for money is anything but easy. You have to remember that when you don’t ask for anything, 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 complaining about your bills. It’s all in the focus.

With men you meet through a sugar daddy dating site, it’s a matter of who takes over first. Do not wait any longer to talk about what you expect from them. They signed up knowing exactly what kind of website they were on. Your expectations should be a topic discussed very early in your relationship. If you have a short first meeting and there’s no time to bring it up (and should bring it up), talk to him about it before your second meeting. If you don’t, you will have relinquished 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 him 3-4 times a month, $200 each time you meet is a reasonable place to start. For an out of town sugar daddy that you see once a month, aim for $400-500. In either case, you can make your contributions gradually increase.

Now, if the man in question is someone you met “on the street,” he may not even know he’s a sugar 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 “hang out with your friends.” Next time, maybe the “his car needs some work.” Make sure he’s not a mechanical genius if you choose that one (unless your car really needs work and you don’t mind him doing it). It will come to anticipate your needs and start freely giving you money on a regular basis.

With any type of sugar daddy, you can work for him to pay your car payment, rent, or mortgage. You can also convince him to pay for you to go back to school or to help you start a business. The key is to overcome doubts about letting him know what you need. Very few of the sugar daddies I have met were shy when it came to what THEY wanted.

Let’s say you’ve been regularly seeing a sugar daddy showering you with gifts, but what you really need is money to pay your bills. After you’ve been dating 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 kind conversation. You might want to start by saying, “I really enjoy spending time with you. I love that you buy me x, y, z. But I could really use some help with my rent, mortgage, or car payment.” Judge his reaction to that request and choose your next move.

If he freaks out, it’s either because he’s more interested in having a girlfriend than a sugar baby, or feels like he’d be buying your “services” if he gave you cash. You may be able to wear it down 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. In time, you’ll find a man who won’t freak out when you bring up the subject of the allowance. Instead, he will be more than happy to help you.