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


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.


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