Carley and Jon

How We Met

Though Jon and Carley were raised 10 minutes apart in Cincinnati, Ohio and attended “sibling” high schools, they didn’t actually meet until moving to Oxford for college. Jon actually first met Carley in an interview… No not a job interview! He was part of the team interviewing her for a professional business fraternity at Miami University (Ohio). They developed a friendship full of sarcasm and laughter over the next 7 months until a late night at BW3’s with mutual friends changed it all! Jon was talking about how he’s passionate about running, where Carley claimed to also be an avid runner. She didn’t think he would actually follow up with her about this shared “passion”…until he asked her on their first date the next day in the form of a RUN through campus. Despite trying to convince him to watch the Lorax and eat nutella sandwiches instead, she knew she had to go on this run if she wanted to get to know this man she was so drawn to. Half way through, he turned to Carley and genuinely was concerned saying “Wow, you’re breathing kind of heavy! You okay?” where Carley admitted to actually despising running (Sorry not sorry). It ended up being the best night of college, where they snuck into the football stadium, ran the bleachers and laid on the 50 yard line for 3 hours just talking about family life, friends, school, their upbringings, their faith in God and everything else under the sun. A second date was to Sunday mass and the rest is history!

How He Asked

Carley and Jon started talking about their lives together when they were 20, and then again when Jon came to visit Carley while she studied in Luxembourg after just three months of dating, and then pretty much incessantly after that as they continued to grow up together. Carley’s dream engagement had two main asks, one to be completely surprised and two, to have all their family and friends nearby to celebrate! This was no easy feat to pull off because after five years of dating, Jon and Carley had discussed both their and others engagements often. Carley actually went on to Jon’s instagram one day and followed “How He Asked” so he would get an idea of her expectations….and didn’t mention it until after they were engaged. When he found out, he cracked up and said “I was wondering why all these beautiful rings and stories started popping up on my feed!!!” Jon knew that he had to start planning far in advance in order to align the schedules of more than 50 people he knew Carley dreamt of celebrating with. Additionally, Jon knew that he had to balance keeping his plan a secret with ensuring friends/family had their schedules blocked off to be in Chicago on Memorial Day weekend!

On Saturday, May 27, 2017, the Chicago sky was completely blue with bright and warm sunshine. Carley’s two childhood best friends, Emily and Danielle, were in town for “the long weekend” with Emily’s boyfriend Jayson. Being that these three people are the closest people to Carley outside of her siblings and family, it was so special to spend the entire weekend with them as they hid this massive secret.

After the most relaxing day with her best friends and a full 2.5 hours to get ready (the most relaxing thing to Carley), the group of 5 friends were in an Uber officially on their way down to Olive Park in Chicago. While on Lake Shore Drive, Carley claims that she was just filled to the brim with anticipation. What if he proposes? What if I’m just over thinking everything? She bowed her head and prayed while looking out at the lake – she was asking for guidance to feel present no matter what was planned for the evening. Well, while Carley was occupied praying, her own parents DROVE BY the uber in their own car! Jon panicked and swung around to start telling a story to distract Carley, who luckily had NO idea they were even in town let alone right next to her on the highway. Carley only knew that she was going to dinner at a rooftop restaurant named Cite with her friends because “Danielle’s uncle recommended it.” After arriving at Cite, Emily suggested the group go grab the perfect picture to instagram because it was such a gorgeous day. It seemed odd that the group would go take a picture despite already being late for the reservation, but Carley is always down to “do it for the insta.”
Little did Carley know that Jon had lined the lakefront path with 25 individual signs each sharing a unique reason he wants to spend forever with her – each one including a picture of them both, the date it was taken, and an inside joke about that particular moment in time of their relationship. As the group neared the beginning of the signs, Carley noticed her friends had stepped backwards. Jon walked to her side, grabbed her hand, and subtly suggested the two walk towards the trees. When Carley looked down and saw the first frame hanging along the water with the city skyline dancing off the water behind it, she dropped to her knees in tears of joy. She stood up, looked over her shoulder, and with simply a look, she and her two best friends in the entire world shared a moment. It was as if they were nudging her, “Go on, it’s time to say Yes to the man of your dreams.” At the end of the path of frames, there was a little alcove overlooking the city. Carley was so excited she didn’t even notice the huge heart of red candles and gorgeous bouquet of red roses in the middle. Jon led Carley to the middle, shared his heart to her and asked her to spend the rest of their lives together!

Carley's Proposal in Olive Park - Chicago, Illinois

Where to Propose in Olive Park - Chicago, Illinois

After quite literally screaming “YES!” over the song Despasito that was playing in the background from all the yachts in the lake, Carley jumped into Jon’s arms! About a dozen of their dear friends jumped out from hiding and completely surprised Carley by sharing how they had set up the entire thing for the last four hours! Little did Carley know, this was the first of many surprises Jon had up his sleeve that night. As she walked into dinner, she saw her and Jon’s entire families were sitting at the table and had all traveled in from Ohio. When she saw her big sister had traveled with her newborn baby, her eyes filled with tears! After an amazing dinner, everyone asked Carley where she wanted to celebrate. They knew her too well because she suggested beers back on her rooftop at home and even hinted at something “small” with a few friends.

Wedding Proposal Ideas in Olive Park - Chicago, Illinois

Engagement Proposal Ideas in Olive Park - Chicago, Illinois

Upon getting home, she ran to her room to kick off her heels and throw on sandals. She was so confused why Jon kept insisting she keep her outfit and heels on and join him on the roof….until it clicked. “Oh, I bet a few of our college friends are up there!” NOPE, Jon had 75 of their best friends all waiting on the roof with the reasons he loved her framing the perimeter and champagne galore. Everyone had flown in from around the country, completely sweeping Carley off her feet again. I mean, Jon went as far as refusing to tell anyone how he was proposing because he wanted Carley to have the feeling of telling people how it happened and having them genuinely be hearing it for the first time so it was more memorable. After mingling for a few hours at the party, a trolley showed up and took everyone around the city to Jon and Carley’s favorite bars to top off the night!

Needless to say, Carley will never forget that beautiful summer day or the once in a lifetime moment they shared with each other and their closest family and friends! To this day, she claims this is the first experience she had where she truly wished she could stop time. She could freeze time looking down at Jon as he asked her to be his wife and just live in that moment forever — luckily for her, I guess she’ll get to do just that by spending forever with him!

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