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.