Find out What This Awkward Proposal Story Has to Do with Chance the Rapper


JAY WHAT DID YOU DO

by Stephanie Kaloi

a couple celebrating their engagement in chicago

Up until recently I was a wedding photographer, and it probably comes as no surprise that I heard a ton of “how we got engaged” stories along the way. And you know what? I think “how we got engaged” stories are some of the best. One of my favorite things about proposal stories is that more often than not, they start with one partner saying, “You know, I was in the WORST mood that day, but (other partner) kept insisting we had to leave the house…”

So when Lindsay sent in her own version of a proposal story, I knew we had to share it. Y’all… this is some “how we got engaged” gold. Our tale begins with this from Lindsay:

I was never really the type of girl that “dreamt” about her wedding day. I mean sure, I may have a Pinterest board titled “Non-Creepy Early Wedding Planning,” but honestly I never seriously put that much mental energy into thinking about it. However, since a handful of my friends have recently become engaged or married, I definitely thought about how I would want my boyfriend to propose. So when my boyfriend, Jay, and I started getting serious, I may have dropped a couple of hints about how I would want him to propose in a very sly, tactful way. OKAY FINE, I flat out made a notes section on his iPhone titled “Lindsay Proposal Notes.” (Yes, I really did this.)

So, what was number one on my wish list for the proposal? I wanted to be surprised. Like, I really wanted to have no idea it was happening until it was actually happening. In reality, I figured I would know Jay was about to propose right before he got down on one knee, but he could at least try to make it a surprise, right? And so our story begins…

Sounds okay, right? Like, who among us doesn’t have a notes section in our partner’s phone with tips? Tooootally a regular, average thing to do. (Note: I don’t do anything with my partner’s phone, but that’s okay! Maybe you do.)

She continued:

I was convinced Jay was going to propose in February. I had caught him texting my friends right before we were going on a trip to New Orleans, and at the airport I got a fortune cookie that read, “There is prospect of a thrilling time ahead of you.” “I KNEW IT!!” I thought. And I was prepared. I had my nails done and a new outfit for every day of our trip.

Well, New Orleans came and went and Jay didn’t propose. But I wasn’t worried, because he told me that he had a big surprise for me on Valentine’s three days later. My parents got engaged around Valentine’s Day so I was sure this was it… until the “big surprise” turned out to be Jay making dinner for me at his place. So then I had the very non-dramatic reaction of deciding I was never going to get engaged.

Fast-forward to a month later, on a really cold day in Chicago. I had just finished volunteering and was running late to meet Jay for brunch. On my way to the door, I ran to the bathroom to brush my teeth. Upon walking into the bathroom, I saw… the most horrible thing. My roommate had three friends in town for St. Paddy’s Day, and one of them had gone to the bathroom in my toilet and didn’t flush. Or use toilet paper. And it was disgusting. I quickly went to flush the toilet—AND THEN IT CLOGGED. This was my worst nightmare. You guys, I buy toilet paper exclusively on Amazon because I am too uncomfortable to buy it in a store, so having to deal with someone else’s bathroom situation was basically unbearable. I grabbed my roommate, explained the situation, told her, “ForTheLoveOfGodPleaseHandleThis,” and got the hell out of there to meet Jay.

And that, my friends, is the story I was passionately telling Jay, right before he proposed to me.

a couple walking before a surprise engagement

That’s right—you see that photo above this text? Are you imagining that this couple is engaged in sweet lovey-dovey nonsense? No. They are not.

As we began to walk by the Lake Michigan, glistening in the sun, I lovingly said: “YOU WILL NEVER BELIEVE WHAT I FOUND IN MY BATHROOM.”

As we passed the secret photographers: “THEY DIDN’T EVEN USE TOILET PAPER.”

As we walked under a beautiful pavilion and Jay stops walking and turns to me: “Seriously, they must have been sick or something because it was DISGUSTING.”

I am missing all social cues that Jay has stopped walking, there is a photographer ten feet away, we are under a beautiful pavilion and something big is happening. I am just too busy having feelings about shit and nothing else matters.

Jay, meanwhile, has zero idea what to do. Upon realizing I am never going to stop talking, he leans close to me, puts his hand on my shoulder and says, “Lindsay, I’m going to need you to shut up for a minute.” And he gets down on one knee. (Nicholas Sparks, feel free to contact our agent.)

a man proposing during a surprise proposal

So after Lindsay realized what was happening, and that maaaaybe the Bathroom Situation wasn’t the worst thing in the world right now, she kind of lost it:

I always thought I’d do this whole “hand-to-the-mouth girl move” out of complete surprise that the love of my life wants to marry me. Little did I know, it would be in absolute horror as I tried to shove all my words back into my mouth.

As usual, Jay didn’t miss a beat. He began:

Jay: Lindsay, I have loved you for 427 days. Do you know the day I knew I loved you?

Me: NO?????

Jay: Thanksgiving of last year.

Me: Yes!

Jay: Uh, wait. Hold on.

Me: [Everything goes black]

Yep, I apparently said yes twice before Jay even asked me to marry him. I do not remember this because I blacked out the first time I said yes. Seriously. I cannot remember one single sentence from the (assumed) sweet speech Jay had prepared. All feeling left my body. I didn’t really come to until the big moment when Jay says…

Jay: “So I wanted to know if you would make me the happiest man in the world…”

Me: ****Okay, that’s a little cliché but whatever, here it comes, I’m freaking out*****

Jay: “…Will you go to the Chance the Rapper Concert with me?” And he pulls out two pieces of paper with printed tickets on them and hands it to me.

proposal story with chance the rapper ticketswoman pushing a man down during a surprise proposalwoman pushing a man during a surprise proposal

…Chance the Rapper tickets?! JAY HOW COULD YOU CONFUSE THIS SITUATION LIKE THIS?! From Lindsay:

And this is when the Best Day of My Life turned into the Most Conflicted Moment of My Life. DO I ACT DISAPPOINTED OR HYPED? I mean, I know I’m supposed to be pissed he didn’t propose, but your girl REALLY wanted those tickets. So I’m clutching the tickets in excitement but also am beyond confused and am trying to figure out if this is all a big prank or if we are actually about to get engaged. Again, all feeling leaves my body and I black out. Apparently I push Jay. No really, I pushed him to the ground and started to walk away, which once again puts him in an interesting predicament. Does he stand up? Go back to a kneeling position? What is the protocol???

Don’t worry guys. There is picture proof I walked back over. Jay reassumed the kneeling position. I yelled at him, “WHAT IS GOING ON?” He laughs and says, “Well, wait. It would be so much better if you went to the concert with me as my fiancé. Lindsay, will you marry me?” “Blessings” by Chance the Rapper starts playing, and Jay pulls out the ring.

a couple celebrating a surprise proposal together

Of course, all’s well that ends well: Jay and Lindsay took photos, and then headed to brunch… which turned out to be a low-key celebration party with twenty-five of their friends.

Moral of the story? If at any point you decide to steal your boyfriend’s phone and to give him very obvious clues on how to propose to you, think long and hard about if you actually mean what you’re saying. Because you might end up talking about unfortunate bathroom incidents pre engagement… but you also might end up with Chance the Rapper Tickets. At the end of the day, I have pretty much locked down Jay for life, so I think I came out on top. Thank goodness, #JayTookACHANCE.


The Info:

Location: Chicago, IL

Stephanie Kaloi

Stephanie is a photographer, writer, and Ravenclaw living in California with her family. She is super into reading, road trips, and adopting animals on a whim. Forewarning: all correspondence will probably include a lot of punctuation and emoji (!!! ? ? ?).

[Read comment policy before commenting]

  • S

    Lindsay has some serious storytelling skill! This is great!

  • Sarah

    concert tickets and a ring? Cool!
    Chuckling though: I was never really the type of girl that “dreamt” about her wedding day. What does have a Pinterest board and putting notes in someone’s phone mean?!

    • a few

      I think that is the new era of having a giant wedding binder before you are even engaged!

    • CMT

      If we could ban “I was never the type of girl who . . .” I’d be happy.

  • theteenygirl

    This gave me the laugh I needed on a Friday morning. Amazing.

  • Kaitlyn

    This was such a great way to start my morning. Also, I def blacked out when I said “yes” too. I had to ask J if I even responded or if I just took the ring hahaha

    • theteenygirl

      Haha I blacked out as well. It wasn’t until I called my mum and she asked what happened that I realized I had blacked out and couldn’t remember if I had responded. Apparently I didn’t even say yes I said “yeah” whoops

  • Green

    Laugh out loud hilarious! Congratulations you, two!!

  • Kat

    This whole thing was a roller coaster and I loved it. Congrats!

  • Sara

    The picture of you pushing him is hilarious. I love everything about this!

  • Julia

    This is my older sister and soon to be brother in law! ☺️ It was such a fun proposal!! Jay even got some of Lindsay’s closest friends who live in other states like Texas/Utah/Kentucky to fly/drive all the way to Chicago to be a part of the big day!! He had everything incredibly well planned!

    • a few

      AWESOME!! He’s going to make a great BIL!

  • another lady

    so much awesome in this whole situation!! my sister’s boyfriend (now husband) ‘fake’ proposed several times leading up to the real thing. they were living long distance with the ultimatum that they needed to get engaged before they moved in together. the move in date was getting closer and closer and no ring had appeared. on a weekend trip before she was set to move in with him (or not if he didn’t propose), he kept getting down on one knee and then asking dumb questions as ‘practice’ (“will you… go out to dinner with me?”, “will you… walk the dog for me?”, etc.) So by the time that he was actually proposing later that weekend, she smacked him and said, “this better be the real thing or I’m going to kill you”! And it was and she said ‘yes’! But, it was not the ideal lovey dovey story that people wanted to hear! lololol

  • Kate

    Please frame that picture of you pushing him to the ground

  • Alyssa

    I love this. More stories like this please! Especially on a Friday!

    • Yael

      Can we all just share engagement stories now? Because I think mine is hilarious and never plan on letting my partner live it down.

      First of all, I had been asking him (in half joking ways) to marry me for at least a year before we got engaged (so, we had been together for less than a year when I started, but I knew he was it). When I was accepted to grad school in Germany, we knew we weren’t going to immediately go there together, because he needed more teaching experience. We also knew we weren’t going to get engaged before I left because we wanted to see how we handled the distance.

      My first trip back to the States was the day after the election, for a conference in Miami. A flew down to meet me, so he got to have a nice, if angsty vacation while I worked, but at least we got to see each other. Sunday afternoon, we went to Miami Beach for a nice lunch and talked about the state of the world/our relationship. We realized we were both just as committed as we had been, and both knew that there was no one else we wanted to watch the world disintegrate with than the other. So as we’re in the back of the Lyft on our way to the hotel to pick up our luggage and head to the airport, not to see each other again till January, I turned to him and said “Marry me.” To which his response was “Are you serious?” I replied that of course I was serious, and I wanted to spend the rest of my life with him. He said he didn’t want to get engaged, because he didn’t want to have to do all that complicated engagement stuff (???? beer cozies were mentioned. Apparently his fraternity brothers all ended up with wives who were *very* into engagement parties and planning *all* the things for their weddings. So, not APW people). So we’re debating the meaning of engagements and whether or not being engaged means we’ll have to start losing our minds and the driver, who is probably paying more attention to us than to where he is going, gets lost. So now we’re lost in Miami trying to get to the airport so A can catch a train to Fort Lauderdale or something to make his flight and we were already cutting it close with the time and then we get to the airport and he had to buy tickets and we’re tearfully saying goodbye because we won’t see each other again for months and….. we never finish the conversation. He never says yes (or no, for that matter). And then all hell breaks lose in the world and I’m trying to finish the semester and a MONTH goes by before I finally realize he never actually answered my question (or demand, as he refers to it). So I call him one night and I’m rather upset because if he had asked me I would have OF COURSE said yes immediately and why didn’t he say yes to me? Doesn’t he love me? Doesn’t he want to be with me? And more of his reasons about being terrified of a stressful engagement and wedding planning and so on comes out and he says “You know I want to marry you. Why isn’t that enough?” To which I responded “Saying you want to marry me is a wish. Getting engaged is a promise.” Apparently those were the magic words because he promptly said yes, at which point I think we both started to cry and then I emailed my best friend because of course I did.

      And that is the story of my month-long proposal.

      • Cellistec

        That story is a modern rom-com waiting to happen. I’d watch it.

        • Yael

          I shared your comment with my partner and asked him who he thought should play me. He suggested Katherine Heigl. The engagement is clearly OFF :)

          • Cellistec

            Actually, I was thinking Mila Kunis, who has such a knack for making talking to herself sound completely normal.

          • Cellistec

            Edit: …because talking to oneself during that suspenseful waiting period would be so important to the plot, not because of any judgment I have about the practice. Which is good, considering I do it myself. ;)

          • Yael

            Looks around, whispers to self, “doesn’t everybody?”

  • Amanda L

    This is phenomenal! I mean, I kind of hate that he psyched you out first, because that’s what my H did to me, too, but it kind of does make the actual engagement THAT much more exciting! Congrats :)

    ***gratuitous proposal story*** I had read all the clues and KNEW we were getting engaged on a Friday. Most likely after dinner at a hotel my then-bf had booked for a staycation (without asking me). So I was prepared with a pretty dress and clean nails for that night. After we checked in to the hotel around 1p in jeans and t-shirts, I said I was going to check out our patio/balcony. Two mins later, bf follows me out and this happens:

    Him: um, I don’t know where your grandmother’s ring is. (You know, the one he was supposed to be taking the diamond out of for my ring).
    Me: um what? (inside: holy shit, did the jeweler LOSE MY GRANDMOTHER’S DIAMOND?)
    Him: I don’t know where your grandmother’s ring is
    Me: ….Sits down in the nearest chair and is freaking out…
    Him: That’s okay though because I know where the diamonds are ***flips open ring box***
    Him again: What do you say?
    Me: You haven’t asked me anything!
    Him: Oh!! Will you marry me?
    Me: Yessssssss!

    Smooth as hell but holy crap did he scare me! Turns out, he’d planned a surprise engagement party for that night after dinner, so that’s what I had gotten wind of! <3

  • Lindsay

    I have officially seen into the future because this 100% sounds like the kind of thing that would happen to me….

  • Abs

    That is pretty much the opposite of what I wanted in a proposal, but wow this story is gold.

  • Pingback: Find out What This Awkward Proposal Story Has to Do with Chance the Rapper | Wedding Adviser()

  • jessikast

    I usually never comment here, but I’ve popped in to say you need to get Lindsay on board as a regular contributor. Her writing is hilarious and so engaging (ha!)!

    • Julia

      I second this!! In the meantime, you should follow her blog listenclose.org ☺️

  • Marie Tachouet

    So great!! L, I feel like we could be friends because I would TOTALLY be telling my fiancee about poop or something amidst the romance. I also love the parka engagement pictures because Chicago (I live there, too:) Congrats!!!!

  • Kelsey

    10/10