A Romantic Windy City Engagement Shoot [We Snuck Onto A Dock!]

I drove up to Chicago this weekend to celebrate Emily and Stephen’s engagement! It was a gorgeous day — so we drove over to Lake Michigan and took some celebratory engagement photos!

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Stephen proposed while he and Emily were on vacation. Their vacation spot was also off Lake Michigan, but seven hours north. Stephen told me when he got down on one knee to propose, he had this whole speech written out.

However, Emily immediately started bawling (happy tears). He said he still tried to fit in some of the speech he worked so hard on, but realized it just wasn’t going to work out because Emily was so excited and couldn’t stop crying. Maybe he can save the speech for the wedding?

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The ring is gorgeous — with a deep blue sapphire in the middle. Stephen really wants to tell Emily how much it cost, but she says she wants it to be kept a secret! The world just may never know — but it is stunning!

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These two couldn’t make each other stop laughing. This is probably one of my favorite poses — Stephen was supposed to be whispering sweet nothings into Emily’s ear, but the word he was actually whispering to get her to laugh is NSFW. So, just enjoy the photo instead! 🙂

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And, sometimes, I’d be trying to pose them — and this is what would happen. This is definitely not how I instructed them to stand! I’m not sure if they’re going for a Rosie the Riveter vibe or what.

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So, I just … let it happen. You’re welcome, world.

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This is the pose we were actually going for —

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Emily and Stephen are native Chicagoans. Emily loves everything about Chicago. So, when we found this backdrop around Montrose Beach — we had to hit it up. Emily can even tell you what the four stars on the Chicago flag mean!

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We also hit a part on the lake with a bunch of fancy yachts. Emily told me the gate is always locked and that you need a card and code to get inside. We watched a woman leave — and it just so happens the gate didn’t lock. #wesosneaky

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A few photos on the dock never hurt anyone, right? We did at least make sure it was locked on our way out, though!

I had originally envisioned the two of them on a cute canoe on the water. Emily kept trying to tell me the water was just too choppy — but I didn’t believe her until I actually saw it! Definitely better to just hang your toes over the edge!

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Later that night, we all went out for drinks. At one point, Stephen was outside waiting for our Uber. Emily looked at me, and giddily declared, “I just feel like I found my person, you know? He loves me for me!” It was just too precious for me not to share!

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Congratulations, Emily & Stephen! I can’t wait to be there for your wedding!

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