When You’re About to Ask

A journal entry from before I proposed

When You're About to Ask | APW (1)

 I’m going to ask B to marry me tomorrow. A couple days ago I was sitting in a brewpub with my friend L, who set me and B up, telling him what I have planned later that week. I had to tell someone. I tell him I’m excited—and incredibly nervous. I doubt B would say no, L says he thinks it’s basically impossible, but nonetheless—the thought of that crumb of a smidgen of a chance that he would turn me down, and the aftermath of that, is just completely fucking terrifying.

Me: “If B says no, we’re going to the nearest brunch place with bottomless mimosas and getting fuckin’ SMASHED.”
L: “But what would poor B do?”
Me: “K can take him to get wasted at a different mimosa place.”
L: “Okay. We can divide up the friends that way.”
Me: “Yeah! And then we can have a drunken rumble in an alley later!”

How does society just expect guys to propose, like it’s not a big deal for them, like there isn’t angst and effort involved, figuring their girlfriends probably made them engagement chicken and have been waiting with bated breath for a proposal for ages? (Seriously, Internet, we need to have a talk about this.) In so many engagement stories, the focus is on the romance and the surprise—the vulnerability of the asker is an afterthought, if that. Do men just not blog enough about it? I scoured the Internet for people writing about the period between when they decide to ask and when they actually pop the question—men OR women—but I could hardly find anything.

Well, I, at least, am excited and anxious and wound up. I couldn’t wait until our vacation in March, my original plan. I could barely wait at all after the rings arrived in the mail!

I’m also worried about the proposal being good enough. Balancing the need for romance and glamour with the fact that our relationship is pretty down to earth and B’s kind of a mountain man—how do I guarantee that I won’t be sweaty or muddy or hungry or gross-looking when we reach SCENIC FOREST VISTA?

An additional wrinkle is that B has been proposed to before, and while he said no to his ex for unrelated (good) reasons, I still feel a bit of a need to top what she did. Organizing stuff like this sends my latent perfectionism into overdrive, googling and plan-B’ing and overthinking things in an ultimately futile effort to make everything go smoothly. How can I ever have enough control over this to ensure it’s the MOST ROMANTIC THING we’ve ever done?

Does the engagement proposal have to be the most romantic thing we’ve ever done to be good enough?

And all of that comes before the worries about what people who aren’t B will think:

  • That I’m a girl asking a guy. (Even in our rather feminist circle of friends, we’ll be the first to do that.)
  • That my guy told me he’d prefer it if I asked. (Yeah. We’re freaking weird.)
  • That I still haven’t found a job. (Working on it.)
  • That I bought both our rings—and our rings are made of silver. (Short version: I’m low on cash, I knew what I wanted, B doesn’t know how he’ll like wearing a ring, and I wanted the option to only “out” the fact that we did it Sadie Hawkins style to the people we wanted to know—which meant buying both rings at once.)
  • My ring doesn’t have a “rock.” (My ring’s literally tying the knot, how more wedding-y can you freaking get?)

But after all the antecedent anxiety in the planning stages, at this point I’m running low on worries. After listing out all the above, I find I’m truly out of fucks to give. Fuck diamonds, fuck perfection. I wanna get hitched.

I hope he says yes.


The food on our date was mediocre. The forest vista was completely obscured by fog and we got rained on. It was definitely NOT the most romantic thing we’ve ever done. He said yes.

Featured Sponsored Content

  • Marie

    Congratulations! And kudos on helping to change the currently dominant proposal narrative one Sadie Hawkins style, silver-ringed proposal at a time.

    • M.


  • Kara Davies

    Are you kidding me? A marriage proposal in the rain?! THAT’S SO ROMANTICAL!!!!!! Congratulations! :D :D :D

    • Karen

      Ha, I also was proposed to in the rain! It didn’t actually feel SO ROMANTICAL because, you know…it was cold and we were wet and I had my hood up and I’m pretty sure I wasn’t looking so cute…BUT we were in Italy overlooking the ocean, so that part was super romantical. Looking back, the rain did make it fun.
      Perhaps not so fun was my response of “Are you serious?!?!” which prompted an awkward, “Umm, yes, I’m serious?” Apparently that is not the right answer – saying yes right away would have been much preferred (so I was later told). For the record, I did say yes after confirming that the question was a serious one!

      • Amanda

        I wasn’t proposed to in the rain, but my response before yes was also “are you serious?!” I think it was just because I wasn’t expecting to be proposed to on our trip.

        • Dani

          Haha, mine was ‘For real? Is this for real?!?’ but, in my defense, were were in a loud, greasy brewery in Montana watching Murder By Death play live. One of those ‘did he say what I think he said?’s because I couldn’t hear worth beans.

      • KerryMarie

        My response: “are you seriously doing this right now?!”….I hadn’t expected him to be able to surprise me, and he did!

  • Eh

    My husband was so nervous when he proposed and that’s part of the fun of our engagement story. I had been bugging him for months to get new glasses and he went to pick up his glasses on a Friday on his way home from work. The store was really busy so he decided since he had the time he could look at engagement rings at the jewelry store a few doors down in the mall. He wasn’t intending on buying – he was just going to look – but he found one he liked and it was the right price so he bought it. I had had a hard day at work and I was exhausted. When he got home I pretty much told him that either he was going to make supper or we were getting take-out because I was not cooking. He made supper. It turns out he was planning on coming home to make supper and then he was going to propose (he normally doesn’t make supper so if he had offered I would have realized something was up). He decided not to propose because I was in such a crummy mood. That evening he was very on edge (the ring was so close and had powers over him). At one point he sat as far away from me on the couch as he could. Saturday morning he let me sleep in, and he got up, did the dishes and made pancakes (I knew something was up because I insisted that he didn’t need to make breakfast but he banished me from the kitchen). He tried making heart-shaped pancakes but they didn’t turn out (he said they looked like bums) – so proposal attempt number two was foiled. Before he went to work on Saturday he asked if we could go hiking to our favourite lookout Sunday morning. I pointed out that we had a lot of errands to do on Sunday before he went to work (plan number three blocked). On the Sunday morning we were lying in bed and he pulled the blankets over his head and cocooned himself in them. I commented on him being antisocial so he cocooned me in the blankets with him. We were just talking under then blankets. The light that was filtering through was warm and soft. Then he told me to not move and he crawled out from under the blanket. I could hear him open up his dresser drawer and I could hear the sound of paper crinkling and him unpacking something. Then he came back under the blankets and proposed. I said yes and I asked him why he chose that moment. He said it was us just being us. Then he told me about all of the other proposal attempts.

    When my husband tells this story it has a hero’s journey type vibe with me being the villain foiling all of his proposal attempts.

    • jashshea

      1. This story made me happy teary.
      2. Bum pancake proposal would have been the BEST story.

    • Ariel

      Way to make me tear up!

    • Totally tearing up here at work!

    • Crayfish Kate

      “He tried making heart-shaped pancakes but they didn’t turn out (he said they looked like bums)” Cutest funny thing! Or is it funniest cute thing??? Whatever, I’m dying!

    • Lauren

      This story is eerily similar to mine. I knew my fiance had bought a ring but I didn’t know the plan or date of the proposal (he insisted he surprise me). One Friday night after work, he came home with all the fixings to make a lovely dinner, a plan which I promptly ruined by telling him there was a work event I had to go to and he needed to come with me because I was too irritated to go alone. We went to said event, it was awful, and I was in such a sour mood on the drive home that I demanded we get take out for dinner because I no longer felt like cooking. He obliged, and we spent the rest of the evening with Netflix. Saturday we were up early and drove two hours to Portland, where we met out-of-town friends for an early Thanksgiving. Fiance was quiet and not his normal self, which I attributed to the fact the Thanksgiving was being held at a stranger’s house (a friend of our friends), who was very unwelcoming and just plain odd. We drove back late and at one point he asked if we could please make dinner the next night, as he didn’t want the fish he bought on Friday to go bad. I told him I had a very busy Sunday planned with lots of work to do (I’m a grad student), and I’d probably have to work through dinner. But I’d see what I could do. I worked all through Sunday morning and afternoon, then dashed off to hot yoga. When I got home, he was cooking but I didn’t even stop to say hello because I sorely needed a shower; once out of the shower, I dressed in my finest leggings and sweatshirt (no bra, of course), whereas he’d put on clean pants and an nice sweater. He put a plate in front of me, and while I was distracted by talking about how good the fish was, he slipped off and came back with the ring, only to blurt out, “I can’t wait any longer!” Turns out the poor guy had been planning our romantic Friday evening for weeks (he’d hidden the champagne in the trunk of his car, made plans to meet our friends for celebratory drinks), and when the plan was spoiled he carried the ring around for days.

      I said yes immediately, and in the next second felt HORRIBLE when I realized how the weekend had gone. He was so worried that it was anticlimactic, but then I remembered a conversation we’d had around the exact same dinner table, two years prior. He’d said, “If I propose, I want it to be just you and me, in our house, eating dinner, doing what we do. I want it to be us.” And that memory turned me into a puddle of tears and I blubbered out that story to him, which he had totally forgotten. I love that despite all of the misfires, everything ended up being ridiculously perfect. Then we drank the whole bottle of champagne and watched “Homeland.” And that’s just one reason why I’m marrying him.

  • Emma Klues

    Whew, so glad there was an addendum on this one to tell us what happened! I never had a rock, my ring is a very simple titanium band and I love it. And our proposal was arguably the least “stereotypically romantic” thing we’ve ever done. Congratulations!

    • M.

      “And our proposal was arguably the least “stereotypically romantic” thing we’ve ever done.” Ours too (Friday after work on the couch in pajamas with computers). I love hearing all sorts of proposal stories, but the ones that just come of a genuine moment and genuine knowing yourselves as a couple, perfect or romantic or not, are my favorite.

    • Jecca

      Haha. Same. He asked me to hold his martini so he could grab his cigar lighter. Then he got down on one knee, and my first words were, “Holy shit!”. We laughed so hard. Later we realized he never really asked and I never really said yes.

      • M.

        When we called M’s mom to tell her, her first words were “holy shit holy shit!!!!” :D love it. an appropriate reaction!

  • PurpleHeather

    Lovely post! My fiancee decided to propose, and realised that there was a perfect opportunity the next week, when both our families would be together, as his family lives overseas, so we don’t see them much.
    The week between him choosing my ring and being able to propose was apparently horrid. He phoned my dad to tell/ask him (which I’m happy about, because my family adore him!) and my dad’s advice was to go to the pub and have a pint, so he could calm down. He couldn’t resist telling colleagues, or he would have burst!
    The proposal ended up being on a path in the rain, with our families nearby, not quite what he imagined at all, but it was lovely. Don’t worry about the sweaty-muddiness, neither of you will remember that!
    And my engagement ring is silver with amethyst, and we’re making our silver wedding rings this summer. Silver is a fabulous metal, I have a silver ring that I’ve worn daily for a decade. It still looks fab. Silver develops a patina and shows age, but that age is the stories of your relationship over time.
    Best of luck!

  • Kendra D

    My husband proposed to me while we were curled up in bed after he had spent a long day at work. No ring, because we’d already decided we would pick it out together after we got engaged. I think he escaped the anticipation and nerves by proposing the minute he decided he was ready to marry me. I had also told him a few months prior that whenever he was ready to ask that my answer would be yes. While it didn’t contain the most romantic of trappings, it was definitely a hugely romantic moment in my life. It was the moment my partner decided not only that he wanted to marry me but that he couldn’t keep that to himself at all. He was busting at the seams with it so he proposed. It was absolutely us and I wouldn’t have it any other way.

  • M.

    Love this. Congrats!

  • Alyssa M

    Our “proposal” moment was so obvious, had been discussed so much before, there he never really asked and instead of saying yes I said “can I put it on?!?” But he was still shaking with nerves as he opened the box. It doesn’t matter how assured the answer is, planning out a moment that will permanently change both your lives and declaring your heart so boldly is scary!

    • ItsyBit

      It doesn’t matter how assured the answer is, planning out a moment that will permanently change both your lives and declaring your heart so boldly is scary!

      Exactly this!! My fiancé and I talked about marriage so often before we were engaged (he even caught me looking at wedding stuff online a month before he proposed) so he knew what my answer would be… but he was still shaky and nervous and vulnerable and had a few false starts before he could get the words out. It’s a big, big thing to hold your heart out like that.

  • Ariel

    Congratulations! I proposed to my fiance as well and it was definitely not the most romantic thing we’ve ever done, but we both love it all the same. We only got one negative comment about me proposing to him (and really, shouldn’t you think before you’re typing a text?). I’ve said my story in the comments before, but it turns out my fiance was planning on proposing the same week and had the ring with him (he got a survival strap – boy likes to take off work and go hiking alone). After I proposed, and he said yes, he said, “you really couldn’t wait a day or two?!” and then I said something like, “you were planning something? What the hell?! I’ve been so nervous about this for nothing? I didn’t sleep last night! You got off easy!”

  • Megan

    Yay! Congrats to you, and well done! Also this:

    ‘That my guy told me he’d prefer it if I asked. (Yeah. We’re freaking weird.)’

    Nope, not weird. One morning over pancakes (we went through a phase where all of our Serious Conversations were over breakfast carbs) my (now) husband and I were discussing where we were in our relationship, and that we both felt ready to get married, and he said, “I’d really like to ask you.” And I said, “That sounds awesome. Would you like to get asked?”

    I say that clear, explicit discussion of feelings, wants, etc. is a fabulous way to start a marriage. Good for you, and congrats again!

  • nightravyn

    I’m another girl who proposed to her guy. My two employees basically smacked me on the head and said “ask him already! He’ll say yes!” 24 hours later, I’d made a comic using xkcd (ty creative commons licensing), sent it to him when I saw he was online (the modern version of passing notes in school, and yes the comic had check boxes for yes and no)… And waited. Nothing. 6 hours later I was ready to throw up. He came home, and I’d finally had the realization that my guy, as brilliant as he is, usually completely fails to see notices that he has email. /facepalm. So I begged and pleaded with him, while trying to not seem like I was begging and pleading, to go check his accounts. “Right after i shower!” /headdesk

    I fell asleep from stress on the couch. He finally check his accounts and I woke up to hearing typing on my laptop next to me. He passed me the laptop, and that’s when I saw he’d scrawled an X through the yes check box in MS Paint. That’s when I burst into tears, then smacked him in the leg, yelling “how the hell do guys do this?!” Since he’d never proposed to anyone, he had no good response to that.

    So yeah been there, done that. I had expectations that I put on myself. Its turned into one of those stories that friends of ours poke us to tell to new friends and we laugh about now. And really, it was something that was completely us: stressed, forgetful at times, heartfelt, internet savvy, and full of laughter at the end of it. ;)

    • KC

      That is incredibly, incredibly cute. And also, yay for people who are willing release things under creative commons for reuse so that cute proposal stories can happen!

    • Crayfish Kate

      This is friggin’ adorable :-D

  • Lindsay Rae

    My fiance is very traditional and I knew he wanted that responsibility and privilege of popping the question. You’re right though, no one talks about the anxiety that anyone asking faces between deciding to ask and The Moment.

    My poor guy, our proposal date (our anniversary) was pushed back by Hurricane Sandy. Originally I was going to have to work, in the end though we spent the day volunteering and he said he would rather celebrate our anniversary the following weekend. Funny enough, after volunteering we were out at a bar and I got upset with him because I just felt that it would NEVER happen (cue the beer tears). He told me after that he was freaking out because he couldn’t tell me that not only would it happen SOON, but it was supposed to have already happened that day!!

  • AG

    Congratulations! This is a lovely story and I know you weren’t alone in your anxieties and hopes.

    Our engagement was lovely and romantic, and did not go at ALL as planned. B’s original plan was to propose on a morning beach walk while we were on vacation. Except, we’d stayed up way late with some friends (and, uh, drinks) the night before, and when he suggested a walk the next morning I croaked “Bleeeggghhhhh” and went back to sleep. It took several naps and a giant order of cheese fries for us to finally recover, and that night he proposed on the roof deck of our beach house. A proposal and cold champagne (and cheese fries!) make for a pretty good hangover cure.

  • enfp

    Yay, congrats! Love this post. My guy also told me he’d prefer it if I asked. I didn’t think this was weird at all. He was ready to get engaged before I was, so it made sense for me to ask when I was ready. I was also DYING of nerves before I did it – even though I knew he wanted me to ask. The proposal was not the most romantical thing we’ve ever done. Sometimes I get insecure that it was not a big enough statement. I am a perfectionist and I was worried that due to all the pressure to make it the most romantical thing ever that I would never actually get around to it. I was just so excited, I wanted to do it soon without going through months of planning. I’d hope that asking someone to make a lifetime commitment is inherently romantic, without necessarily making it a huge production, but the pressure to go all out sure is intense!

  • This is EXCELLENT.

    My husband proposed to me in our bedroom, after work on a Monday, while I was mid-post-work-clothes-change, bugging him about where we wanted to eat since we were in the midst of packing for our pilgrimage home for Christmas. The glamorous romantic notion of proposing is silly and ridiculous for us. In my mind, if big surprises and showy plans are already part of your relationship (I have a friend like this), then great! Your proposal perhaps should be a big to-do, but if you’re like us and that’s not an integral part of your relationship, it seems silly and disingenuous.

    Also: my wedding band is silver. Way cheaper than gold and allowed us to afford stones in the band. My husbands band is tungsten and it cost $54 dollars. We are planning to buy a second “winter” band for when it’s cold and his fingers are swollen with summer heat.

  • Class of 1980

    Me: “If B says no, we’re going to the nearest brunch place with bottomless mimosas and getting fuckin’ SMASHED.”

    L: “But what would poor B do?”

    Me: “K can take him to get wasted at a different mimosa place.”

    L: “Okay. We can divide up the friends that way.”

    Me: “Yeah! And then we can have a drunken rumble in an alley later!”

    That conversation made my day. ;)

  • StevenPortland

    I loved the how this story ended with that short addendum. Almost like an afterthought — “he said yes”. Congrats!

  • Ashley Douglass

    This is super sweet. I got lucky in that my asking was a spur of the moment thing, but also I knew how he would respond. He had asked me drunk a couple months before, the night of the government shutdown, because he was worried about his health insurance. The next day, sober, we decided we weren’t quite there and since there was no worries about insurance we should wait a little, but we also joked about who would be the one to “win” and get to ask first. Then for those next couple months we joked about it, and talked about it, including things like rings, with him jokingly saying he wanted a blood diamond, and me getting him giant red ring pops and jokingly asking. This continued as the conversations got more serious and at one point about a month before he asked what I would say if he asked right then, and I told him I still wasn’t ready. Another month passes, we had a relaxing night at home, and as we are crawling into bed I ask, because I finally feel ready. He says yes and we head to bed. The next day we wake up and discuss if we were joking the night before, or if we are really there, and that is when we realize we are both ready and we begin to call our families. It was low key and silly and perfect all at the same time. Plus I “won” by asking him.

    • Jenna

      Roomie, is that you? :)

      • Ashley Douglass


        • Jenna

          Oh hooray!

  • Amy Elizabeth

    Yay! I proposed to my guy and am always thrilled to read others stories about it! He also told me he’d like me to propose. Well actually he declared at 3am after he’d been working late and I was mostly sleeping that “he’d decided” that when it was time for us to get engaged he wanted me to propose. “And, I want romance!” he said! LOL. The pressure!

  • lady brett

    i *love* the addendum

    • Jess

      Somehow, it was my favorite part. It was funny and sweet in its simplicity and honesty.

  • Hazel

    I love hearing stories about other women proposing! I joke my proposal was a surprise for both of us and its mostly true. We were long distance and he was visiting, and we had been joking about being “conditionally engaged” the night before. The next day we were cuddling and talking and I just had the overwhelming need to ask him if he wanted to be married to me. I then realized that would be proposing and freaked out. I kept telling him that I wanted to ask him a question but was nervous, and went through a couple rounds of that before finally getting it out. He said yes :)

    The reactions I get from those hearing our story are usually some version of your are so modern! etc. and I find it a little bit annoy. However mostly the people who know us reasonably well weren’t that surprised that I asked, and were really happy and enthusiastic for us.

    We spent the next week or two looking for engagement rings for online since he wanted one too!

  • World Proposal Limbo Champion

    I spent months planning and preparing to propose. I even *invented* a completely new (as far as I can tell) type of puzzle box and built it myself (with CNC machining help from a friend 1500 miles away who cut wooden parts from my design docs). Finally the vacation to our favorite place in the world came around, and I was ready. When the power went out, leaving us in the dark at our oceanfront condo, it was perfect! I asked her to walk out to the pier with me… and her dad decided to join us. (Her parents were on the same scuba trip.) Well, so much for that.

    I went back to my original plan, and later in the week, it was all set. We had a great evening (without her parents), and near the end, I pulled out the puzzle box safely wrapped in a double-thick sleeve I knit myself out of chunky, fuzzy yarn and tied with leather straps to look like a Christmas cracker. She took it and announced her pleasure at the workmanship of The Device and its packaging. I was planning to get all speech-y reminisce-ish whatever while she worked the puzzle… but, *knowing what was inside*, she put it back in its sleeve and put it away.

    Um, what on earth does it mean when someone accepts an engagement ring, knowing what it is, and keeps it but doesn’t *open the ring box*? Well, I’m currently in whatever limbo that is. Basically, the proposal has been started but not completed, and I’m really, really confused. (Perhaps when we go to my youngest sister’s wedding at the end of next month, that’ll jar loose whatever’s stuck. Or not? I hate waiting, but for now, at least, it beats the alternative.)

    • Alyssa M

      Perhaps ask her what it means? I would guess she A) isn’t ready to say yes, but doesn’t want to say no, or B) doesn’t actually know what’s inside or C) maybe she has a surprise planned for you! Either way it sounds like an open line of communication is whats needed….

  • Nicole Cherae

    1) Super sweet. Congrats!
    2) Our engagement story, like so much of our relationship, was just a conversation.
    3) This post made me ask my fiancé about his own in between period. He said he was nervous and terrified about asking and realizing that he wanted to spend the rest of his life with me.

  • Guest

    I developed a raging migraine on the day my guy proposed to me. I mean a head pounding, too nauseous to eat, really want to go home and curl in the fetal position migraine. And he had planned all this stuff. I tried really hard not to wreck it for him, but it’s hard to hide a migraine. So instead of going to a fancy dinner, we ate (well, he ate and I picked at food) at one of our usual haunts, I bought Advil and Tums, and he took me home to sleep it off. And then when the pain stopped a few hours after dinner, he returned to Plan A and proposed. He said later that he didn’t want to wait too long for another auspicious occasion to propose, so he was really glad when the Advil finally kicked in. :)

  • clairekfromtheuk

    Another proposer here (waves). Although technically, when I think about it, I didn’t so much ask as inform him that we were getting married :)

    I knew I was on pretty safe ground though as he’d already asked me at least four times before I was ready

  • Erin

    I haven’t even had a chance to finish the story yet–so excited to!!!–but I’m DYING over the freaking engagement chicken Wikipedia page! “Engagement Chicken is a lemon and herb flavored roast chicken dish, purported to cause boyfriends to propose marriage.” I can’t even.