Proposing Part 1: Why you should propose to your boyfriend

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Will You Marry Me Vintage Silverware Hand Stamped Sugar Spoon by AnvilDesigns
Will You Marry Me Vintage Silverware Hand Stamped Sugar Spoon by AnvilDesigns

One of the things I learned from my reader survey was how many of you identified yourselves as “ladies in waiting,” i.e. women biding their time until their boyfriends propose. Well, girls: STOP WAITING! If you're into questioning traditions, start by questioning the very first assumption about weddings: that a woman's role is waiting for a man to pick her.

I know: it's scary right? You're thinking, “What if he says no?” Well, no one said taking your life by the reins would be easy, and the anxieties and fears of rejection that come up around proposing give you great insight into some of the cultural pressures men traditionally experience.

Proposing is definitely scary, and I'm speaking from personal experience here. As those of you who've read my book know, I actually proposed to Andreas …

On our third anniversary, we went to this pottery painting place. As I'd planned, I painted a big plate with a picture of us holding hands. (Yes, we were naked in the painting. I like painting butts!)

Above the little people, I painted the words “Psst: will you marry me?” Then I put my grandmother's diamond wedding ring onto the plate and slid it across the table to Andreas.

He looked at the plate. He looked up at me.

I looked at him. Nothing happened.

“…Well, will you?” I said.

“Of course!” he said, and I exhaled in relief.

“…But you don't mean, like, IMMEDIATELY, right?” he said. “I mean, of course we're spending the rest of our lives together. But there's no rush, right?”

“Er, I guess not…” I said.

“Awesome!” he said. “I love you!” And then he went back to painting.

I sat and freaked out a bit, but nothing had really changed: we were still just as committed and someday we would get married. Just not quite yet, evidently.

“No rush,” in our case, meant getting married three years later.

Grab the traditional institution of marriage by the balls and tell it that you're doing this on your terms and in your own way.

This is all to say that I know that it's scary and intimidating and hard. (It should be noted that Andreas has expressed feeling sort of bad for how he handled the proposal. I mean, it all worked out ok, but it wasn't the stuff of swelling violins and magical twinkly lights.)

Of course not all men want to be proposed to, and you know your boyfriend best … I'm thinking that chances are good that if he loves you for being a sassy independently-minded offbeat girlfriend, he's the kind of guy who would appreciate tipping an old tradition on its ear.

When you propose to your boyfriend, you're taking a huge first step toward grabbing the traditional institution of marriage by the balls and telling it that you're doing this on your terms and in your own way. It's an exercise in taking ownership of your life and your journey through it. It's your way of saying, “I'm not going to drop hints to get what I want — I'm going to apply that energy to building the courage to do it myself.” This isn't just about proposals. It's about knowing what you want and feeling strong enough in yourself to just go get it.

This isn't to say that it's not a wonderful thing when men propose. Ideally, any proposal is the result of many conversations about what marriage means to both you, why you're committed to each other, etc. It should never really be “popping the question.”

But if you've had conversations about commitment and you're ready to get married — STOP WAITING!

Read part 2: How to propose to your boyfriend

Comments on Proposing Part 1: Why you should propose to your boyfriend

  1. I think women proposing to their boyfriends is a fantastic idea, but I don’t know how well that would fly with most men folk. I am always surprised when my young hip heterosexual friends hit snags when it comes to things like taking your husband’s name, which last name to give the kids, and wives that make more money than their husbands. I thought we were over all that?
    The male ego is a delicate thing, so I would agree with you when you say you know your boyfriend best and how he might take a proposal.

  2. My wife proposed to me. We had pretty much decided to get married by then and I guess I was dragging my feet. So she got me a ring and one day while we were snowboarding at Mt. Baker (a very special place for us) she asked me to take a break on the side of a slope and then pulled out the ring and asked.

    I thought it was incredibly cool, romantic and a great surprise. I almost lost the ring in the snow while showing it to my snowboarding buddies later in the day :O

    All the male friends I was with at the time also thought it was cool.

  3. Last year, on February 29, I asked him to marry me, shyly, after explaining that Feb 29 is the one day women are “allowed” to propose. He said no. 🙁

    Don’t get me wrong, it was good! I was looking to commit, but I think I was more in fantasy land than reality at the time. That rejection precluded a very bad spot in our relationship where we almost split. I spent that time staring at the proverbial mirror, and I found I wasn’t happy with the way I was, and I set to make some changes; and so did he. We learned we couldn’t live without each other.

    Then, nearly 8 months later, he asked. And this time we were both ready. 🙂

    I really like that plate!

  4. I asked my guy to marry me. I knew he would say yes — we lived together, he kept slipping and calling me his wife when introducing me, etc — but I was still terrified doing it. And impatient. It was supposed to be on a beach in a place that meant a lot to me, I wound up doing it the night of my brother’s wedding, when we were in varying stages of undress.

    Had he been the type to take offense at it or have his ego wounded by this gender-role switcheroo, I don’t think he’d be the guy I want to marry.

    • Hello,

      My name is Brooklyn Bagwell and I’m a Casting Director for Sharp Entertainment. We’re casting for a new groundbreaking documentary series about women proposing to men! We’re currently looking for women who are planning to propose to their boyfriends in the near future. Is this you?

      I would love to chat with you more about this! Please let me know if you or anyone you know would be interested in this casting call.

      You can email me back on [email protected]

      Brooklyn Bagwell

  5. Although there wasn’t much of a proposal, and he bought me a ring, if I had waited for my husband to point out that we should get married, I’d still be waiting. It pretty much went like this.

    Me: “I want to get married in California. Let’s get married.”
    Him: “OK, let’s do it sometime.”
    Me: “How ’bout next summer?”
    Him: “OK.”
    Me: “I want a ring, or people at work will bother me about it.”
    Him: “Great, I’ll buy a cheat one on ebay.”
    Chorus: “Yay!”

  6. Also: “Had he been the type to take offense at it or have his ego wounded by this gender-role switcheroo, I don’t think he’d be the guy I want to marry.”


  7. I was considering proposing to my Man about six months ago and after going to a wedding where he had a little too much to drink, he let it slip that he “had a plan.” I decided that I wanted a plan too, so I went and bought him a ring and waited for him to ask first (I didn’t want to step on his toes). On New Years Eve (i.e. last week), he proposed to me in New York (at the Cloister’s Museum), after about five minutes of giddy excitement and picture taking, I got down on one knee and asked him back. He was so surprised he forgot to answer and put the ring on his finger. I reminded him, and of course he said yes. We are now in the throws of wedding planning! It all worked out quite well.

  8. I was on the verge of proposing to my mister, but he beat me to it =] We’re offbeat, yes, but the traditional part of me was kinda happy to have that moment.
    Several of my female friends proposed to their misters, and I think it’s wonderful. As you said, why should women wait to be picked? Sure, it’s nerve-wracking, but it’s the same for the men out there who propose.

  9. I WAS planning on proposing to my boyfriend. We had been talking about it (marriage) for awhile but I knew how he could be about making decisions so I figured I should take the lead on this one. But I have a big mouth and I let it slip that I wanted to propose to him. Turns out HE wanted to propose to ME too. So we have decided to have a super secret engagement ceremony weekend. We’ll say a few words and exchange gifts and then announce it to the world. I’ll let you know how it turns out. 🙂

  10. I proposed to my husband. We hadn’t talked about marriage at all, and I surprised even myself with the proposal. We had just started a conversation about all the mushy things we like about each other and he asked me if I would change anything about him. I told him I would change one thing. I said I would make him my husband instead of my boyfriend and that was that! He clarified that I was actually proposing and when I said I was, he accepted! rules, schmoolz

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