He gripped the box. He held the tiny cube firmly in his hands as he paced back and forth. It was almost a routine at this point. He stood in the cool shade to hide from the sun for a couple of moments and took a few steps toward Lake Michigan to look around. From there he’d make his way back to the shade to check his phone and her location. He was nervous. He was excited. He was impatiently waiting for her arrival because he was about to pull off the best surprise to date. But before she got there we tried our best to ease his nerves and chatted with him about anything and everything. We asked Jack why proposing is such a nerve-wracking experience, especially assuming that he knew Olivia was going to say yes. He took a deep breath and chuckled as he told us that it’s not about asking the question, but about making it the perfect experience and moment. He just wanted her to be happy. Pausing for a moment to say that our hearts absolutely melted, and it wasn’t from the heat wave of the day. That was the sweetest response we could have anticipated and we literally watched his perfect plan unfold right before our eyes. As he was talking to us his nerves turned to excitement that he couldn’t contain. She was there. We watched her walk along the lakefront without a clue as to who was waiting for her. But then she spotted him. She threw her hands up in the air in confusion as to why Jack was walking towards her. He got down on one knee and she said the happiest and easiest “YES!” ever.

Perfection. Complete perfection is the only way to describe this moment. When we tell you that Jack went all out for this surprise, we’re not kidding. To give you a little backstory, Jack is currently stationed in Texas while Olivia still lives in Chicago. To Olivia’s knowledge, Jack was coming into town the following day. But she was so wrong. He made sure she got the day off of work, had friends and family involved in helping surprise her, picked one of their favorite spots at Belmont Harbor, and even went as far as using an app to create a fake location on the off chance that Olivia checked his whereabouts. It was all too good and Jack pulled it off effortlessly. That’s why we love this moment leading up to Olivia’s arrival. It’s emotional. It’s raw. It’s the perfect example of what it means to love someone with your whole heart. Jack wasn’t nervous for the fear of hearing no. He already knew that he and Olivia are destined to be together forever. Jack was nervous because he loves her so much that he wanted to make the proposal as memorable as possible. Her happiness is his happiness. And man, she was so happy. She cried happy tears and was honestly in such shock it took her some time to even process the events that just played out. They both embraced each other in a long hug with their smiles stuck on their faces. It was just the two of them surrounded by the hustle and bustle of the lakefront, soaking in all the joy and love together. Pretty incredible if you ask us. 

Olivia and Jack, still screaming congratulations to you as you enjoy your engaged era! Thank you, Jack, for letting us be a part of the surprise. And thank you, Olivia, for smiling through the excitement and happy tears as we celebrated with some portraits. You two are truly such a beautiful couple. We love how much you adore one another and are in awe of what great lengths you will go for one another. Such a strong and magical bond and we cannot wait to see what the future holds for you as you begin this next chapter of your lives. Cheers to forever!