What Does It Mean When a Sugar Daddy Gives You a Ring?

QUESTION: I recently started a bit of a fling with my very own sugar daddy. It’s been four months of expen­sive din­ners, fancy gifts, limo rides, shop­ping sprees, and spa days.  Last night at din­ner, he slipped me a lit­tle blue box from Tiffany & Co. It was my first piece of jew­elry from him and it was a dia­mond ring. I don’t think he was propos­ing, but I don’t think it was just “jew­elry” either. But how do I know for sure?

CHELSEA SAYS: Did he ask you to marry him? If he didn’t actu­ally say the words, “Will you marry me?” or some­thing along those lines, then it would be way too pre­sump­tu­ous to assume that your sugar daddy was pop­ping the ques­tion. So, you’re right about that one.

It doesn’t really sound to me like drop­ping money on expen­sive jew­elry is as big of a deal to your sugar daddy as you think it is. He clearly likes spoil­ing you with expen­sive gifts, so what’s one more? But I still think you should acknowl­edge it if it makes you that uncom­fort­able. Don’t make it complicated—just ask him what the ring means and what his inten­tions are in this rela­tion­ship. Does he think you’re in a seri­ous monog­a­mous rela­tion­ship, or is this strictly a sugar daddy/sugar baby fling? I’ve found that older busi­ness­men types tend to favor con­ver­sa­tions that are direct, even blunt. So don’t be afraid to just go for it.

How­ever, if you’re going to go down that path, you should prob­a­bly also know what you want out of the rela­tion­ship. If he turns around and says that he’s look­ing to set­tle down with some­one, but you’re just look­ing for a rich sugar daddy to spend money on you, then tell him that so you can part ways and move on to some­one who’s on the same level as you. It can go the other way too. If he says it was just a gift like the oth­ers and he’s just hav­ing fun with you, but you want some­thing more, you may also need to recon­sider why you’re with this sugar daddy of yours. In any case, hon­esty is the best pol­icy here.