“I want to propose to my man. (I’m a woman.) How should I do it, or should I?”

Let’s start by providing something that will actually get used: an e-mail address for hate mail: [email protected]. Your question enthralled us. In 18 words, you sent a bolt of lightning to the very heart of gender roles, stereotypes, and cultural norms. It’s such a simple question with such a thorny, unsettling answer. To risk a false dichotomy, we have deep sympathy for the extremes of either position:

1) Sure, what the hell?!?! We live in an enlightened time. Love, chemistry, and relationships transcend outdated, insulting, and misogynistic “rules.” We’re smarter than that. We’re better than that. So, eff tradition–go for it.

Or…

2) You’re eating his balls for breakfast.

The truth, probably, falls somewhere in between, and it depends a lot on you, your relationship, and your potential man-bride. Now before we hit the rocky shores of gender roles, you first need to think about the proposal in general–regardless of who’s doing it–and wonder if you’re ready. Every good proposal has two components: the discussion and the ritual. They’re two very different things.The discussion, whether explicit or in code, happens days or weeks or months or even years before the ritual. The couple gets a sense that yes, together, jointly, they’re ready for marriage. Regardless of the asker’s anatomy, the first commandment of popping the question is simple: the answer shouldn’t be a surprise.

Have you had the discussion? Again, it could be an explicit conversation or, more likely, an oblique and subtle game of where-are-we-going-with-this. If not, have it. That’s your first move. We would give you this advice whether you’re a man or a woman.

Assuming you’ve had it, then there are (at least) a few possible scenarios:

He’s dragging his feet. He’s waffling. He won’t commit. It’s fish-or-cut-bait .
You’re both in. Now someone needs to step up to the plate.
He’s gung-ho to get married, but you’ve been standoffish, and now you’ll surprise the hell out him by proposing.

In the first scenario, you’re really just trying to give him an ultimatum, right? If that’s the case, then you’re using the ritual to steamroll past the discussion. If you want to give him an ultimatum–and, depending on the circumstances, there are valid reasons for doing just that–it’s more honest to just give him an ultimatum. For the second and third scenarios, the discussion is over, you know he wants to get married, and now it’s a question of the ritual itself.

Like any tradition involving men and women, the man-proposing-to-woman is arguably unfair, irrational, and discriminatory. Perhaps hundreds of years from now, people will look back on this Neanderthal custom, shake their heads, and marvel at our barbarism. There’s a fine line between chauvinism and chivalry, and everyone sketches that line differently. This gender role might be outrageous and insulting, but whether we agree with it or not, we need to recognize that it exists. Even if your guy is self-assured and strong and secure in himself, well, there’s a chance–okay, a pretty damn high chance–he’ll feel that you’re mowing his lawn.

Ultimately, it comes down to this question: what’s your boyfriend like? Many guys would be flattered-as-hell. But many more guys, I suspect, regardless of how amazing and intelligent and sexy and spunky the girl is….and regardless of how good-natured and progressive and feminist-friendly the guy is…might still resent–secretly, perhaps–having the proposal usurped. (Then again, he’s had his chances to propose and he didn’t, right?)

If you’re filled with unshakable confidence that your guy is above this BS, well, maybe you’re right, and in that case, go for it. Only you know the answer to that. But this bears repeating… Be unflinchingly honest with yourself about that calculation. A lot of guys seem progressive and open, and a lot of these same guys–including me, probably–still cling to certain elements of tradition, and this one’s a biggie.

In any case, we admire your guts and attitude. Please let us know what happens.

Good luck.

-The Plunge