What I Learned From Proposing To My Boyfriend


In all the recent discussion about proposals and getting engaged, I kept wanting to talk about women proposing to men. I proposed to my boyfriend on Christmas Eve, 2008. Proposing as a woman is still unusual — not an idea most people consider. But proposing taught me a lot about myself, about our relationship, and about engagement/marriage. I asked Meg if I could write a guest post, and she wrote back “DO IT! I’m totally into it!” So, here goes!

Things I learned from proposing marriage to my boyfriend:

  • What marriage means to me. It all started when I realized I really did want to get married. I wanted to say out loud “We intend to be partners for life.” We were planning a life together, already making all our major decisions together. I wanted the world to recognize our committed partnership for what it really was. Since we both knew it, why not say it out loud and in public?

I also wanted us to be recognized as a family. All the legal stuff really matters to me. I wanted to say to the world: “We’ve chosen each other as family. We’ll share property, protect each other, and trust each other to act for us.” Marriage was the way to accomplish that.
  • The cultural narrative about getting engaged is crazymaking. We’re told that a man doesn’t want to get married, until and unless he makes a surprise proposal with a ring. We’re told that if a woman brings up marriage, any later proposal doesn’t count — he’s just doing it to appease you. We’re also told that if he really loved you, he’d propose right away, before it ever occurred to you to wonder when he was going to propose. Women are told both that the proposal means everything, and that we have no control over whether or not it happens. No wonder we feel like we’re going crazy.
  • I had a horror of becoming the stereotypical girlfriend, nagging the guy to get married. In Kamy Wicoff’s book I Do But I Don’t she unflinchingly describes the roiling mix of frustration, anger, guilt, and anxiety she felt waiting for her boyfriend to propose. I was similar. We’d watched a friend wait and wait and wait for a proposal that never came, hinting and teasing and nagging to no avail. Her boyfriend seemed to relish the power it gave him; he’d hint that he was going to propose, and then not follow through. I didn’t want to play that game. But I was already playing it in my head.

My boyfriend would make some remark about weddings or getting married, and hope would spring up — maybe he’s planning a proposal! Then he wouldn’t ask, and I’d be disappointed and angry. Then I’d feel guilty for being angry, frustrated about the whole situation, and finally just feel like I was going crazy. Why was this such a big deal to me? Why couldn’t I just calm down and let things happen naturally?
  • The woman shouldn’t be stuck just waiting. While watching that friend wait, we’d agreed either member of a couple should be able to ask. So added to all the other emotions, I had the icky feeling that I wasn’t living up to my own statements about equality. And I wondered if he might even be waiting for me to ask. So I started thinking about proposing to him. I wanted to change the story.
  • Changing the story can be hard. it can seem like everyone is pushing back. I googled “women proposing” and talked to my friends. There was one clear message: “Cute idea, but you should really wait for him.” 

One of my closest female friends told me “Men will propose when they are ready. We just have to wait for them.” A close male friend just couldn’t envision how a woman proposing would work. The internet told me that he’d feel like I was stealing his thunder. It also warned me that he might say yes without meaning it, just to keep the peace. Some articles warned me that it would ruin the relationship forever.

The warnings didn’t ring true to me, not for us and our relationship. He isn’t a big-surprise kind of guy; no thunder to steal. With really important things, he always speaks honestly. He wouldn’t say yes if he didn’t really mean it. He’s not particularly traditional, so he wouldn’t be offended by my proposing. And those conversations about weddings and getting married — the ones that had made me think he might be planning to propose — told me that yes, he was thinking about marriage. He was ready. I didn’t have to wait for him to propose to know that.

And while I trust my friends, their warnings weren’t based on anything specific about me or my boyfriend. They were talking about how they thought a proposal should go. 

The more I thought about the assumptions and expectations behind all the warnings, the more I realized: I could propose. It would really work for our relationship. I bought a man’s ring.

But all those warnings still sat in the back of my mind, having a party with the cultural narrative. They kept popping up to tell me “You’re doing it wrong!” I spent several more months agonizing, which brings me to my next point:
  • Proposing is scary. When you seriously contemplate standing in front of someone else, and asking them “Will you marry me?” — well, it’s terrifying. You’re incredibly vulnerable. You’re really asking them “When it comes right down to it, is this relationship everything you want it to be? Can you do this for the rest of your life?” It made me realize that a man might delay proposing even when he’s sure he wants to get married, just because actually spitting out the question is terrifying!

When you’re a woman proposing to a man, you get to add to those questions, “Can you handle the fact that I’m asking? Do you have unspoken expectations about gender roles in our relationship that I’m breaking?”

I’d felt ready to be proposed to for a couple of years. But when I faced actually proposing to him, I was scared. Totally terrified. It took me months to get up the nerve. I even came close to losing it at the very last minute. I’d set up a romantic Christmas Eve at home, had the ring all prepared (box wrapped like a present), love songs playing. I wanted him to know I was serious — that I’d planned this and thought it through. 

But as the evening went on, I started panicking. “I shouldn’t do this,” I thought. “I should wait for him to do it. He’ll think I’m desperate. He’ll pity me. He’ll say yes to shut me up. It’ll be a huge disappointment.” All completely ridiculous in the context of who he is and what our relationship is. But that big, vulnerable moment has a big unknown right after it, and the existing cultural narratives were trying to fill it up.

Even deeper, I worried “What if, somehow, I’ve got it all wrong? What if somehow he’s really not happy with me? What if I ask him, and he realizes he just can’t do this anymore? What if he says no?” 

When the moment came, though, I found myself just doing it. It felt like I was moving on automatic. All the worrying about what I’d say and what he’d say — just gone. There was nothing but the moment. I grabbed the ring box and gave it to him, kneeling in front of him. Confused, he opened it, then stared at the ring. “Are you trying to —” he said.

“Yes,“ I said. “Will you — do you want to marry me?”

“Of course!” he exclaimed, and kissed me.
  • Post-proposal reactions may not be what you expect, especially for a non-traditional proposal. There’s no script. I wasn’t sure what to expect: questions, confusion, ambivalence? Instead, he was overjoyed, grinning and giddy. Me, I cried and shook. All that anxiety and adrenaline was taking its toll. It took me a long time to calm down.

Announcing it to other people was almost as scary as proposing, for me. Would they accept an engagement where the woman had proposed? Would they be excited for me? There was no script for this announcement — no sticking out my hand with a ring on it and waiting for reactions.

I saw this in my parents‘ reaction when I told them “I have an announcement to make. Last night, I proposed, and he said yes.” They hugged us and said “Congratulations,” but they looked kind of surprised and confused. I was, honestly, a little disappointed. Deep down, I’d been expecting jumping up and down, excited squealing, all that stuff. I’d been hoping for it, wanting validation that it was okay and acceptable that I’d proposed.

Since then, they’ve shown that they’re thrilled, happy and excited about our engagement and wedding. But just as there was no script for my announcement, there was no script for their immediate reaction. There was no “ZOMG let me see the ring! Tell the story!!” They were feeling their way as much as I was. That’s just real life. It’s not what you expect from the movies, but that doesn’t mean it’s wrong, or that you’re wrong.

Proposing to my boyfriend meant changing a deeply ingrained cultural narrative. That was intimidating and scary. There was pushback, both from other people and from my own assumptions. But it also gave me space to think about who we really are, and what getting engaged and married really meant for us. Telling a new story means you get to examine those assumptions and decide which ones work for you.

If you’re a woman who wants to get married to the man you’re with, I really do recommend at least considering the idea of proposing to him. It may not be right for every couple and every relationship. But just the process of thinking about it will give you a lot of insight into your thoughts and feelings on getting engaged.

Remember: There is no one single right way to get engaged, just as there’s no one single right way to get married. It really is okay to write your own story, no matter how similar or different it is to the existing cultural narrative. I can’t say it’s easy. But it’s worth it.

(P.S. If you’re like me, and process ideas by reading about them, I recommend two books. One is I Do But I Don’t, by Kamy Wicoff, which I mentioned above. The other is Young Wives’ Tales, eds. Jill Corral and Lisa Miya-Jervis. 

I Do But I Don’t is Kamy Wicoff’s personal story of getting engaged and married. She ends up making mostly the traditional, expected choices, but she has a lot of interesting analysis about them. 

Young Wives’ Tales is a highly multivocal collection of essays about marriage, written by all kinds of women. Some are happily married; some regret marrying; some reject the whole idea of marriage; some try to reinvent marriage; some totally subvert marriage. You’ll nod in violent agreement with some, want to argue with others, and still others will leave you totally confused. That book saved my sanity by showing me just how very many different ways there were of thinking about marriage. If you’re feeling squashed into narrow expectations about marriage, Young Wives’ Tales will help you break out.)

Featured Sponsored Content

Please read our comment policy before you comment.

The APW Store is Here

APW Wedding e-shop

go find all our favorites from around the internet, and our free planning tools

Shop Now
APW Wedding e-shop

Planning a wedding?

We have all the planning tools you need right now.

Budget spreadsheets, checklists, and more...

Get Your Free Planning Tools