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"How Do I Tell My Boyfriend NOT to Buy Me a Diamond?"

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Writes Save the Date reader Ana:

I’ve been dating a lovely guy for almost two years, and we live together and everything. I think a proposal might be in the works, which is great.

So here’s the problem: When I was very young—maybe even when I was born—my aunt invested in several loose diamonds so that one day my cousins and I would have diamonds for our engagement rings. (Or some nice diamond jewelry, if we opted not to marry.) So that’s totally awesome.

But how do I let my boyfriend know this diamond exists without (A) freaking him out or (B) seeming like a high-maintenance chick? It would be so nice for him not to have to spend the money on a diamond. I realize this is a total “first world” problem to have, but I’d love some feedback!

Here are my thoughts:

My line is always “open, honest communication,” but I get that saying, “Hey, I have a diamond when you want it—IF you want it—not that I’m expecting a diamond!” feels totally awkward and presumptuous and unromantic. Which is to say, I don’t think you need to say any of it.

Technically speaking, the diamond isn’t yours to hand over, right? I assume your aunt’s still in possession of the diamond, so she should be the one to offer it up. If your aunt’s never met your boyfriend—or that would be a super-awkward conversation (“Hi, boyfriend I’ve met once!)—you could also ask one of your parents or a sibling to mention the rock, maybe via email: “Hey, Aunt Shirley asked me to let you know that she has a diamond she’d love for you to use in Ana’s engagement ring when you’re ready to start thinking about that. No pressure to propose or even to use the diamond, of course, but it seems like that’s the direction you’re headed in, so if you’d like to see it, she’d love for you to email her when the time comes.”

That conversation too could be a little awkward for your boyfriend. But I think it’s the least-awkward alternative—especially if he’s {Yikes! } already ring shopping. It’ll be much easier for him reply to one of them with a quick: “Thanks. I’ll reach out.” then to stammer to you, “Um, are we getting married?” or “Uh, I already bought a ring.”

I think the key to the whole thing not feeling shady or scheme-y is to ask a family member to mention the diamond—and then ask for the conversation to end there. Tell your mom or sister, “Please tell him about the diamond, but please don’t tell me how the conversation goes.”

Ladies, what do you think? Should Ana tell her guy about the diamond? Or ask a family member to step in?

Have a wedding-y dilemma of your own? Email me!


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