Proposing Part 1: Why you should propose to your boyfriend

Updated Jan 12 2017
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

  1. I proposed to my fiance on Christmas Eve 🙂 We've only been together a little over a year but I've never been more certain about anything in my life, and I knew he was the man I wanted to spend the rest of my life with. When we went over to his parents' house for dinner one night, I took his mom aside and asked her for permission, showing her the ring I'd chosen and bought earlier that week. Asking her for permission to marry her son was almost more terrifying than asking the man himself to marry me!
    The staff in the jewelry store went apeshit and started cheering me when they found out what I was in there for! It was the first ring I looked at, in the first store I went to, and I knew it was the one I wanted to give him but I still made myself go look in every other jewelry store I could find in that mall before I made my decision. I didn't find another ring that even came close to the first one.
    In Christmas Eve morning I made up a tasty stew in the crockpot, picked up some of his favorite beer and some wine for me on my way home from work, and we watched the Griswold Family Christmas movie and The Grinch. At the end of the Griswold movie I said I wanted to give him his present that night instead of tomorrow with the family. He opened it up (we were sitting on the couch) and said "oh my god that's so nice….WAIT WHAT KIND OF RING IS THIS, YES YES YES" and then cue copious amounts of water-buffalo noises and tears from me.
    The most terrifying, exhilerating, wonderful thing I have ever done. AND the ring fit perfectly. On Boxing Day we went out and found a ring for me, and we're getting married April 22 🙂

  2. Hello everyone! It's just amazing to know about all experience with the proposing a guy subject. I read so many of your positive stories and experiences and smiled while I was reading most of them, felt so happy for you guys. It's something I was thinking for a while for myself so far, and finding this site and reading this article all together with comments gave me such a support in same idea. Recently I was trying to have a nice talk with my bf and proposed him idea of us marrying, but turned out into a fight, which was heartbreaker for me. I just received the answer that I just want to control everything and that he's not ready for marriage. I was completely shocked since I never presented my proposal idea as a drama and obligation, I said it really nicely and got just gaslight attitude which broke me so badly… I simply don't feel loved even he kept telling me after fight that I just should enjoy his love and how I'm blind to see that he loves me.. it's just, crazy guys, don't know what to think..

  3. I proposed May 25th to my wonderful amazing boyfriend, now fiance. It was our two year anniversary and I'd been planning it since the week before Valentines Day. I made him an "exploding" box, which is a paper craft that the side of the box fall down when you open it and you can fill with whatever you want. In my case it was pictures and cute notes about our relationship. In the center I put a second box (technically the 6th layer) with a lid and attached a string to the lid so that when he pulled it out on the string would be notes with the "words will you marry me?" each on their own paper and a silicone band tied to the end (I wasn't sure he'd wear an engagement ring, but we rock climb so he'll want a silicone one later to alternate with his wedding band. Joke's on me he wears it everyday and totally would have worn an engagement ring had I bought one). His reaction was adorable.
    Shortly after the excitement and kisses ended we looked online and found a great ring for me. Unfortunately due to Covid-19, it won't be here till mid-July, so we amazon'd a silicone ring for me too.

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