How Do I Ask My Sugar Daddy for Something That’s More Expensive Than He Usually Spends on Me?

QUESTION: The other day I saw a really expen­sive designer hand­bag that I absolutely fell in love with. My sugar daddy usu­ally has no prob­lem spend­ing money on expen­sive gifts for me, but this bag costs a lot more than he usu­ally spends. How do I ask him for it with­out com­ing off as being a spoiled brat?

CHELSEA SAYS: There are a few ways to go about this with your sugar daddy. The eas­i­est thing to do is to put on your big girl panties and just straight-up ask him for it. I’m not say­ing go up to your sugar daddy and demand that he buys it for you or you’ll leave him, but just tell him that you saw this bag you really liked and you real­ize that it’s a lit­tle more money than he usu­ally spends. Worst case, he’ll say no. At least then you’ll know what his bound­aries are for future expenses. If your sugar daddy does end up spend­ing that extra money for you, make sure he knows that you’ll be show­ing him just how grate­ful you are to be his sugar baby.

If you’re not com­fort­able just ask­ing your sugar daddy directly for the expen­sive bag, or if you know that it’s really out of his bud­get, sug­gest a trade-in. The next time he buys you some­thing, tell him that you have a con­fes­sion. Explain that you saw this bag in the store and you fell in love with it. Ask him if he would be offended if you held off on this gift and put the money towards the more expen­sive bag instead. Who knows, your sugar daddy might be feel­ing gen­er­ous and you may just end up get­ting both gifts.

If blunt and direct really isn’t your style, here’s a sub­tler, albeit sneakier, approach. Tell him about the bag, but dis­cuss plans to buy it your­self. Tell him about how you’re going to work hard to try and save up for it because, as much as you love it, you know that it’s a lot of money to spend on one item. As your sugar daddy, there’s a good chance he’ll end up step­ping in and buy­ing it for you with­out you even hav­ing to ask him to. He’ll feel like the hero for pro­vid­ing and mak­ing his sugar baby happy. You’ll get the bag and boost his ego, all at the same time—everyone wins.