Kelsey: Proposals Are Tricky

Even more so when there are two of them

I really thought we were going to ace the proposals. We’d saved for rings together, we’d shopped for our rings together, picked them up together, and mutually decided on an approximate timeline. I thought that it might make the actual proposing process easier. At least we both knew that it was coming, and we each knew what the other’s answer was going to be. That seemed pretty major. I worried a bit about the proposals feeling special, and hoped that people would still think our engagement stories were cool. Still, it seemed like it was going to be less stressful, at the very least.

Julie and I each wanted an engagement ring, and we each wanted to be proposed to. Julie suggested that, once we had our rings, we would both know that a proposal was forthcoming and whoever felt moved to propose first, would. I told her that was an amazing plan, and very equitable, and as long as we both understood that I was not ever, ever proposing first, I could see no flaws in its execution. 

Since I thought I had managed to avoid the pressure of a perfect proposal by going second, I was unprepared by how stressful waiting to be proposed to was. I wanted to make things as easy as possible for Julie in order to get the perfect romantic memory we would remember for the rest of our lives. In order to honor the wonderful moment she was surely concocting, I felt like I needed to be proposal ready AT ALL TIMES. I could never be cranky, or tired, or uninterested in any casual suggestions from Julie, because this could be the suggestion or the hour or the evening that was going to lead to the pinnacle of our relationship thus far! I couldn’t express displeasure with anything Julie did because I didn’t want to argue or snap at each other and possibly derail her carefully crafted proposal. Or worse, make her rethink the whole idea of proposing to me at all.

Even with all of my careful emotional choreography, I ended up screwing up her first attempt. I was making dinner and we were chatting one random weeknight, and I mentioned casually that in addition to my scheduled Saturday morning shift at the craft store, I had offered to cover someone else’s Sunday afternoon shift as well. Julie reacted to my announcement in a way that I felt was entirely out of proportion to the facts. She freaked out, and raised her voice, and said something to the effect that she had a big problem with how much time my part-time job was taking up. I was really surprised by her vehemence, and I got defensive. Which for me looks like wounded, condescending, and infallible all at the same time. “We made the decision together for me to work part time.” I intoned haughtily. “You had your chance to weigh in. I have responsibilities to them! I have some integrity!”

It was perhaps not our finest moment. Later that evening I learned that Julie was upset because she had reserved an adorable cabin in the mountains for the weekend and had planned to propose after I got off of work on Saturday, then whisk me away to Boulder where we could eat tapas and sunbathe and bask in our recently engaged glow before we came back to share the news with our family and friends. Whoops. We’d worked hard to make proposing this egalitarian process, a mutual decision, to start as we’d mean to go on in our marriage, and yet here we were. Both feeling pressured and un-empowered.

Julie ended up proposing in the park right by our house where we like to walk with our dog. She packed a picnic with three different kinds of cheese, and bread, and chocolate, and tiny pickles. She had planned an amazingly involved proposal wherein I would take my turn at Yahtzee and roll out my ring along with the dice. In her elaborate picnic packing however, she totally left Yahtzee at the house and ended up wresting my ring out of the pocket of her skinny jeans before she popped the cork out of the split of champagne she had hidden. A year later, I don’t remember what she said to me when she asked me to marry her. I remember her face, and the sunset, and watching the neighborhood teenagers taking prom pictures in the park. I remember drinking champagne out of mason jars until it got too cold to stay outside any longer. Proposals are supposed to be this crazy, romantic, once in a lifetime experience to mark a very important moment. Instead, Julie took an experience we’ve had a dozen times, and made it a special one because she brought together some of our favorite pieces of our normal lives in order to mark a once in a lifetime moment.

We did the best we could planning our dual (dueling?) proposals. But it turned out, proposing and being proposed to wasn’t about the story. It wasn’t even about loving the memory of the event. Some big moments, no matter how you plan for them, are hard. For things that great, joyful, and huge, you can’t always mitigate the enormity with a good contingency plan. Big decisions come with big emotions, and emotions do not care about your plans. The myth is that the dramatic, surprising, showily romantic, Facebook-ready proposal sets the stage for your gorgeous whirlwind of a show of a wedding. The truth is that proposals are a distinct moment where you and your partner make a life changing decision. And in their uncontrollable hugeness, engagements don’t prepare you for a wedding—they prepare you to be married.

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  • Stella

    “I felt like I needed to be proposal ready AT ALL TIMES. I could never be cranky, or tired, or uninterested in any casual suggestions from Julie, because this could be the suggestion or the hour or the evening that was going to lead to the pinnacle of our relationship thus far!” EXACTLY. I think I was permanently dressed up for about a MONTH before the proposal (for some irrational reason I was terrified of being proposed to when I wasn’t PHOTO-READY. Sad but true.).

    • Siobhan

      I knew it was happening that year and freaked out when Valentine’s and my birthday went by with no proposal. Then he proposed on holiday and I was sunburnt (really sunburnt) and we were both a little drunk and it is not the cutest story but I love the memory anyway. It was ours, it is still ours that is all that matters – but having wanted to be photo ready I was *so* not! I had a stripe on my chest from my bag strap and smelled strongly of after sun lotion!

      • april

        Love this! And I have a similar story. After a long day at the beach we went and got dinner and a couple of beers our favorite brewpub. When I got back to the hotel – tired, tipsy, and a little bloated – I pretty much immediately pulled off my jeans and prepared to fall into bed. I believe his exact words were “Put some pants on, april! Let’s go for a walk on the beach.” He proposed on that walk, of course. I may not have been photo ready, but at least I was wearing pants …

        • Caitlin

          This may be my favorite proposal quote ever! Just about spat water across my desk from laughing. This is so cute!

    • This is exactly why my partner and I opted for no proposal. We did much the same thing as Kelsey and Julie: we saved up for rings together and discussed price points. We designed/selected rings, and each held on to one while we waited. We knew we were going to get engaged, and then married.

      But I didn’t want to wait around for a proposal, and he didn’t want me to propose to him instead of/before he could propose to me. So we picked a date that was special to us (the 1-year anniversary of the day we moved in together), and made a fancy dinner reservation. That evening, we came home from work, got dressed up, kissed, cried a little, exchanged rings, took some awkward selfies, and went to dinner as an engaged couple. It was awesome.

      • mackenzie

        @feerless:disqus, I just love this. How special. I love that you had a moment that was for the two of you that didn’t require this crazy element of surprise. My proposal wasn’t anything like yours, but how I wish yours was more the norm. It’s such a big moment to have it just “sprung” on you out-of-the-blue.

    • Natalie

      Hah! I had this exact same fear! I told my fiance at one point, “I really like the idea of it being a surprise but I have to admit… what if my hair looks AWFUL, and you get a photographer and all I can see is how bad my hair looks?!”

    • We totally cheated. We each proposed during some spontaneous, non-glamorous day. Then about a month later we planned an engagecation (engagement vacation). So we made fancy dinner reservations out of town, got super dressed up, and each secretly had the maitre’d help us propose during dinner (me before dessert, him after). We guaranteed that we’d be dressed and prepared for the occasion. And it was great fun giggling through dinner at our “surprise” proposals waiting for us. Bonus: Forest Whitaker was dining at the next table and took our “newly engaged” picture.

      • MC

        This is awesome on so many levels. What a great idea!!

        • It was pretty fun. All the roses, champagne and tears. None of the stress. I honestly think the restaurant staff had more fun than we did. All I asked for was to bring his ring on a plate. They concocted this elaborate rose petals and smoke under a cloche thing! Apparently they don’t do many female led proposals and wanted to go all out.

    • mackenzie

      for me it meant always having photo-ready nails.

  • Meg

    waaait is my reading comprehension bad or did you not describe your proposal to her too?? I wanna know :)

    • MC

      That’s what I came here to say – I wanna know what Kelsey did too!

      • Meg

        saving it for another post maybe :)
        I agree proposals are tricky!! There is something very liberating about planning a lot of the things together up front though.

  • lady brett


    also, i totally “ruined” my honey’s proposal…and, somehow, four years later, reading this is the first time i’ve stopped to wonder what it was she had actually planned.

    i mean, we were planning a nice dinner and a play, so i suspect it was planned for somewhere in that date, and we went on that date anyhow – but as a celebration after i bullied the proposal out of her beforehand (i didn’t *know* it was a proposal when i was being pushy, i could just tell there was a *surprise*. so, obviously the thing to do was say “whatwhatwhatwhatwhat is it?!”)

    • JDrives

      That’s also my response when I know a surprise or prezzie is coming. Drives my fiance batty sometimes!

  • M.

    “Instead, Julie took an experience we’ve had a dozen times, and made it a special one because she brought together some of our favorite pieces of our normal lives in order to mark a once in a lifetime moment.”
    <3 <3 <3 This is my favorite kind of proposal story. It's been described in so many iterations on APW, but proposals that are "ruined", or not a spectacle or take place on the couch in jammies or whatever, it's always so special to see it stripped down to the essence of what is happening in that moment.

    • sara g

      Yes! My fiance proposed at a little cafe in the town where we met, where we had gone almost every Saturday for brunch when we lived there. I had always imagined an epic mountaintop proposal at sunset (or something along those lines), but the way it happened was so much better and more “us”.

      Plus, we got free mimosas. Can’t beat that!

      • Kara E

        If it makes you feel better, I got the epic (?) mountain proposal, on a lake, at sunset, but it was also a normal piece of our lives since we love hiking and adventure. It was lovely, but…us.

  • MC

    Was it at Cheesman Park? That park is one of my faves in Denver, one of the first places where my fiance and I hung out, and I can totally see people getting their prom pictures taken there. Anyway, I love picnics in Denver parks and this is a wonderful piece.

    • Kelsey

      Sure was!! It’s my favorite Denver park too

  • Anon

    I love the idea of incorporating the proposal into what is otherwise an ordinary or typical moment in your relationship – an authentic reflection of the two of you as partners. Love that.

    Our favorite shared activity is camping (we’re huge outdoorspeople), and he proposed during a hike while camping at our favorite spot. It felt true to us, but was made all the more special because of the beautiful surroundings (and privacy!).

  • was the cabin in Boulder by chance at Chautauqua? That’s where we are getting married! :)

    • Kelsey

      You guys and your Colorado hot spots today! Yup, totally Chataqua. What a lovely spot to get married!

  • LydiaB

    “Instead, Julie took an experience we’ve had a dozen times, and made it a special one because she brought together some of our favorite pieces of our normal lives in order to mark a once in a lifetime moment.”

    Yes to making a normal experience special! I had a proposal whilst decorating the Christmas tree in our flat, something ordinary but magical at the same time, it honestly still makes me tear up just thinking about it. I thought I wanted something big and extravagant but I love that now each year as we decorate the many trees we will have, in the many homes we will have it will always bring me right back to the moment he truly surprised me with his love and thoughtfulness.

  • mackenzie

    “be proposal ready AT ALL TIMES!” This. I was told in May (?) 2012 that “another summer would not pass before we were engaged.” And so, every trip we went on, every nice dinner, every night I headed over to his house after work, I had my “propose to me” face and armor on. Not to be disappointed when it didn’t happen, but it felt a lot like living (for months) with bated breath. We got engaged in August ’12 and married 13 months later. It was all wonderful, but that it’s-going-to-happen-but-when feeling can shove it.