Summer Engagement Photos in Chicago

Rachel and Derek share the kind of love that you will feel within five minutes of meeting them! This is one blog post I’ve been particularly excited to share.


Rachel started working at the same company as Derek back in 2017, and the two hit it off at a company happy hour. After discovering that they had so much in common, Derek ended up sliding into her Instagram DMs the next day. He casually mentioned that he watched a couple of the movies she had recommended (so smooth, Derek!). The next day, they met for drinks and ending up talking for hours, watching the sunset from Rachel’s building rooftop. They describe their connection as instant, where they felt like they had known each other for a long time and been best friends.


Almost exactly four years later, the two made their love official when Derek proposed on a trip to Cancun in August 2021. After years of telling Rachel he could never propose on a vacation (fear of losing the ring and all the added nerves), Derek decided this would be the sure way to surprise Rachel with a proposal. Before having dinner during one of their nights in Cancun, they took a walk to the pier for some sunset photos. Little did Rachel know, she would be SHOCKED when Derek dropped to one knee with a beautiful speech and proposed. Friends of the couple, who were also along on the trip, were able to capture the moment and celebrate their engagement. Rachel and Derek walked to their favorite rooftop spot at the resort to take everything in with each other, before calling all of their family and friends.

When asked what makes their relationship special, this is what they had to say:

“We align on all of our core values, we cheer each other on to be our best selves and go for what we want, and we absolutely love spending all of our time together. We have such open communication channels and it’s the best feeling knowing that the other person genuinely understands you. We love our friends and family more than anything, and we are grounded in our faith as our foundation. We have so much fun together no matter what we are doing, and we are always planning for new and exciting adventures. We both know this life has limitless potential for us, and can’t believe how lucky we are to get to explore it all together.”

Rachel says, “Derek is so easy to fall in love with. He instantly made me feel such a deep sense of trust in him, and I knew he was the one at the very beginning. He instantly connected with my friends and family, he was super romantic, always finding ways to make me feel special, and was unwaveringly supportive.” She knew Derek was the one for her with the way he knew exactly how to take care of her when she was experiencing some chronic back problems.

Derek says, “I knew Rachel was the one right out of the gate, specifically the first night we went out together… In addition to her sharing so much in common with me… Prior to Rachel, I was never one to voluntarily head out to the dance floor to dance, yet somehow she was able to get me out there confidently as if we were the only two out there in our own little world. I’ll never forget that, as since then, I’ve never passed up a chance to dance with her, and that’s one of the many things I look forward to the most on our wedding day.” It was clear to Derek that Rachel was a keeper with how quickly she made an impression on all of his friends and family, and he credits her to helping him strengthen his relationships with all of the people closest to him.

The majestic colors of the sky on the night of their engagement session make me SO happy. The first time we had scheduled to take engagement photos, the darkest clouds of doom rolled in just as everyone arrived and parked at Museum Campus. And before we even got out of our cars, the downpour started. It quickly became evident that the storm would not be passing anytime soon. These two could not have been better sports about rescheduling. On the second try, we had the most perfect day! I cannot wait to celebrate Rachel and Derek again this coming August for their big day at the Monte Bello Estate!

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