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.