Karly and Ryan

How We Met

In January of 2017 after recently relocating from Wisconsin to Denver, Colorado, I joined the dating site Bumble, out of pressure from a dear friend (Thank you, Amanda). After much hesitation and doubt, I reluctantly decided to give it a try. Low and behold, one of my first “Swipe Rights” happened to be the handsome, successful, Midwest, Minnesota Nice, Ryan. After talking over Bumble for several weeks, Ryan asked to meet up for drinks. Although it was a fairly casual Tuesday night of drinks, I think we can both agree that it truly was love at first sight! Our time together felt effortless, natural, and sweet. Truth be told, Ryan went home that night to his brother’s house and told his brother’s fiancee, “I’m going to marry that girl someday!” For the next couple of days, we didn’t communicate with each other. Ryan was moving into his first house, and I was consumed with teaching 24 little loves as a first-year teacher. I, being the most overly sensitive girl in the history of overly sensitive girls, thought that was the end of that, and we’d never see each other again (THE DRAMA… I know!).

Engagement Proposal Ideas in Chicago, IL

Proposal Ideas Chicago, IL

But, you guessed it, Ryan ended up asking me out on our first official date later that week! He made a reservation at a quaint Italian restaurant in Denver, picked me up in his, then, red Volkswagen (cute, right?), and introduced himself to the hostess as Ryan Anderson. And, yes, that last detail was HUGE – I was finally able to save his phone number in my phone, as he wasn’t known as “Ryan from Bumble” anymore… A big milestone when you meet from online dating!

Karly's Proposal in Chicago, IL

Our night together was perfect, and although it seemed quick, we both knew that this relationship was the real thing, the one-and-only, the forever. 3 weeks later, I was on a plane flying to meet Ryan’s family for the first time on their annual Family/Friend Ski Trip in Salt Lake City, Utah. As if I wasn’t already 110% sure I wanted to be with Ryan forever, a weekend with his family sure made a girl convinced! I knew, undeniably, that I wanted to be an Anderson for the rest of my life.

Karly and Ryan's Engagement in Chicago, IL

Over the past two years, Ryan and I have been through and experienced amazing things together! From family vacations to marriages inside & outside of the family, to more musicals, and everything in between, there is not a single person I’d rather have by my side as my best friend!

Where to Propose in Chicago, IL

How They Asked

Let me start off by saying that I am a Kindergarten teacher, which means that Ryan and I love to travel together during my Spring Breaks. Two years ago (to the exact proposal weekend), we went on our first trip together to New York City. While we were there, I took Ryan to see his first Broadway Musical, The Book Of Mormon.

Over the course of our relationship, we have grown to love attending concerts, musicals, piano bars, YOU NAME IT together. So… What better way to celebrate Ryan’s 29th birthday then by buying him tickets to see the latest and greatest, Hamilton, in Chicago over my Spring Break! My thoughts were that this would be an exciting weekend getaway and an even better way to continue a tradition set in stone two years ago. And for Ryan… Well, he had some thoughts of his own!

I began planning every detail of our trip to Chicago in early January… Talk about Type A! I reached out to a childhood best friend who “made reservations for drinks Friday night”, planned a day of shopping on Michigan Avenue, and researched all of the local hot-spots for breakfast, lunch, and dinner. If you asked me, I had the whole trip planned down to a “T.” All the while, Ryan was communicating with my family and friends, as he was planning the most unforgettable weekend and the most well-thought-out proposal. In order to paint a picture of how the best day of my life really played out, let me break it down for you this way:

7:00am – Ryan wakes up to workout. WORK OUT ON VACATION? AT 7AM? I thought it was crazy too! He never works out on vacation.

9:00am – The two of us head to Yolk for breakfast right off of the Magnificent Mile.

10:30am – Ryan’s family arrives in Chicago, unbeknownst to me. My parents pick Ryan’s family up from the airport, and they spend the day on Michigan Avenue avoiding us at all costs!

2:00pm – Ryan and I grab Potbelly’s for lunch. Hands down, this is Ryan’s favorite sandwich shop, but as I eat, Ryan doesn’t touch even a bite of his food. He later explained he was so anxious and nervous that he just couldn’t eat!

3:45pm – Ryan’s family and my family are ready in place to watch the proposal from a Core Power across the street.

4:00pm – As I’m getting ready for drinks at The Signature Room, Ryan says that he is going downstairs to the hotel restaurant to grab a beer. “WONDERFUL! Grab me one too, please!” was my response. Again, this was all part of his wonderful plan to make sure the decorations were in place and the photographer was ready for our arrival.

4:15pm – Ryan comes back up to the room, no beers in hand! He says that the hotel is offering free beer and wine to all of their guests on the terrace starting at 4:30pm, and that it would be a great idea for us to go grab one before we leave. Let’s pause here quick. This made me unhappy… I was rushing to get ready, struggling to pick out what to wear, and frustrated that he was changing the plans I’d made so long ago with friends!

4:30pm – After changing my jeans 3 times, slapping on some lipstick, and adding a final touch of hairspray, I was ready to leave. Ryan was adamant that we grab a drink on the terrace, and I was adamant that we leave right away, as we were already late (Yeah, that one is my fault). Nonetheless, Ryan leads me down to the terrace, all the while, I am putting up a stink that he’s asking me to do this.

4:40pm – As we round the corner of the hotel hallway to the terrace, I see through the windows rose petals lining the ground and candles lit across the ground. My immediate response was, “Oh my goodness, I AM SO SORRY!” So sorry for being the most difficult girlfriend EVER!

4:45pm – Ryan asked me to spend forever with him! My response was the easiest decision I’ve ever made. And although I don’t remember every word of his wonderful proposal (HELLO SHOCK!), I do remember feeling on top of the world. The only thing that mattered, then, there, and forever, was us. Him and me. My few fiance!

The rest of the weekend sped by faster than I wish it would’ve, but several things are for sure – my love for him, my love for us, my love for our families, and my love for our happily ever after. Can I get a “BEST SPRING BREAK EVER”?!

Special Thanks

Keith French
 | Photographer