The Engagement Story & Why I Love Our At-Home Surprise Proposal

proposal chicago lakeshore lincoln park zoo

We’ve been engaged for quite a few months, planning is underway, and I realized, I’ve never actually shared our #justsaidyes moment AKA the engagement story! So, settle in, pop the popcorn, because here we go.

If you know Dave, then you would find him proposing on Cinco de Mayo as funny as I do. But Dave’s love for tacos is another story for another time, I suppose. However, I do still believe part of him ended up proposing on this day so that we had to have tacos on our anniversary forever.

Anyhow, it was May 5, 2017. I happened to have a happy hour after work and ended up staying a little longer than I normally do. I was feeling it when I got home and Dave and I decided to order tacos for Cinco de Mayo. Little did I know, Dave had a lot in store for our next day; however, I was about to ruin all of it and change our story forever. Little did I know that Dave kept making big plans for us, but I kept making other plans for myself — friends’ birthdays, galas, brunches, etc, all kept getting in the way of Dave’s proposal plans. But Dave decided the next day, May 6, he was going to take me to the lily ponds in the Lincoln Park Zoo and propose! We would celebrate after by going to the Cubs game (#baseballday is sacred in our house) and then to La Scarola, his favorite Italian place that he’d been wanting to take me to for ages.

Well, I arrived home and we had a glass of wine together. Dave asked me to take a quick look at the menu of one our favorite Mexican delivery restaurants on his phone and pick out my order… he would then place the order as I was in the shower. Well, as I was looking at the menu on his phone, I saw messages popping up from my cousin, Jess. I didn’t look to see what the messages were about, but I was wondering why Jess was messaging Dave. SO when he came back in to get his phone, I asked why she was messaging and he froze. He tried to make up some story about dinner plans since she was coming into town, but I know him better – he never makes dinner plans like that so far in advance. I decided to jump in the shower and he was meant to order the food, but as I’ve been made aware, he had a mini freakout during that 15-20 minutes. You see, Dave was concerned that I thought he was hiding some things from me since he was messaging with Jess and he started calling his friends who tried to talk him down. They told him it was fine and I’d probably forget (which I actually had – wine solves all of life’s problems!), but he couldn’t shake it; in his mind, he thought that I thought he was lying to me and he couldn’t stand that thought. Also, I’m pretty sure he couldn’t handle hiding the ring for another moment longer.

I hopped out of the shower and heard a knock at my bathroom door. Dave asked if he could come in. I was wrapped in towels and just out of the shower, but I cracked the door open. He told me he hadn’t ordered the food yet, but he loved me very much… and the rest of it is a complete blur! I know he said some very sweet things, but all I remember is him being on his knee and saying sweet things, me crying and him asking if that meant yes?! Of course it meant yes! Honestly, I thought he was planning the engagement soonish, but I didn’t think it was this soon. I was thrilled!



engagement tears of joy

Literally crying tears of joy

rose gold engagement ring

Incredibly excited, we then Facetimed our families and closest friends (while I was still in my towel) letting them know all about the surprise engagement! Dave then ordered tacos (I still think this may have been his favorite part of the night) and we ate tacos, chips and guac, and drank wine to celebrate our engagement! The next day, I went out for a friend’s birthday, and then Dave and I then went to celebrate by doing the activities he had originally planned for his proposal (minus the Cubs game cause it ended up being a bit chilly) — Lincoln Park Zoo, drinks at the J. Parker and dinner at La Scarola.

engagement celebration lincoln park zoo


proposal chicago lakeshore lincoln park zoo

engagement celebratory drinks j. parker chicago

engagement celebratory drinks j. parker chicago

engagement celebration chicago j. parker

I’ll admit, this was a completely unexpected proposal, but it was 100% welcome. I mean, I knew it was coming, but I thought maybe eventually in a few months or so. Also, it wasn’t a flashy, crazy proposal with 100 roses or a scavenger hunt, but honestly, I don’t want any of that. None of the milestone events in my life have ever been conventional, so why should my engagement be conventional? This is 100% us, and I love it. Dave says that my cousin’s messages threw off the proposal he had planned, but honestly, I love that my best friend is a part of our proposal – that makes my heart happy. I love that our story involves friends and not strangers. I love that we were home so I could Facetime our family and friends in my towel on the bed with sopping wet hair and be able to laugh when each one asked why I was Facetiming in my towel. I don’t need big flashy displays of affection – all I need is the man I love, some tacos, guac and wine. I couldn’t be happier to celebrate Cinco de Mayo together for rest of our lives!

celebratory brunch chicago engagement family

celebratory brunch chicago engagement family

Celebratory brunch at my sister’s on Sunday with my besties – they were super impressed, ha!

Now I want to hear about your #JustSaidYes moment and so does WeddingWire! They are running a contest and giving away $10,000 towards your wedding. Read more about the contest and enter to win here. Good luck, congrats on your engagement and don’t forget to share your moment in the comments below!

*This post is sponsored by WeddingWire, but all opinions expressed are of my own.

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  1. So sweet! And now I’m tearing up at work. #thanksash

  2. This story is so sweet! I love how authentic it is to your relationship!!

  3. I love your engagement story! It was genuine and not #forthegram
    It will make for a funny story to tell the little Dave’s and Ashley’s.

  4. Every engagement story is fun, unique and filled with so much love!! Can’t wait to follow you on this awesome journey!
    Thank you for always stopping by! xo, Jessica || The Petite Diaries