Holly + Derek’s Milwaukee Engagement Photos

Meet Holly + Derek

Holly and Derek’s love story began with a swipe on Bumble. But their first meetup didn’t happen right away! After some convincing from Holly’s friend, she took the leap and texted Derek to finally make plans. The rest, as they say, is history! Today, they’re living their best life with their adorable pup, Lilo, who’s now a year and a half old.

The Proposal

Derek had been planning his proposal for months—around six or seven months to be exact. He wanted to make sure everything lined up perfectly. For Derek, the big moment would come after one major milestone: graduating college. On the night of his graduation party, surrounded by friends and family (including relatives who traveled all the way from California!), Derek asked Holly to be his forever. It was the perfect, heartfelt moment to celebrate not just a graduation but the beginning of their next chapter together.

Milwaukee Engagement Photos

For their Milwaukee engagement photos, Holly and Derek chose downtown Milwaukee as their backdrop. They had a blast taking pictures at the iconic Milwaukee Art Museum and Discovery World, which perfectly showcased their playful and loving dynamic. These locations offered stunning views of the city and gave their photos an artsy, modern vibe—just like Holly and Derek themselves!

Wedding Planning

Holly and Derek’s August wedding will take place at the beautiful Birch MKE. Holly knew exactly what she wanted—a warehouse venue—but Derek wasn’t entirely sold on the idea. As soon as they walked into Birch MKE, though, they knew it was the perfect place. The venue combines Holly’s love for the urban, industrial vibe with Derek’s desire for an outdoor space. The gorgeous patio and garden, complete with twinkling string lights, felt like the perfect balance for both of them. They can’t wait to say “I do” in front of their closest family and friends!

Dreaming of your own Milwaukee wedding? Let’s chat


Loved these Milwaukee engagement photos? I’ve plenty more amazing to share—find more inspo here!

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Meet Ali!

Your Milwaukee wedding & Senior Photographer

I’m a Milwaukee based photographer with more than eight years of experience and hundreds of weddings and sessions behind me. I love capturing joy filled moments, from wedding days to the excitement of senior year.

I am all about lists, laughter, and ice cream. My goal is to help you feel comfortable so your photos look natural, fun, and uniquely you. From sweet candids to striking portraits, I focus on the real moments that tell your story.

ANP is built on a small and trusted team that shares my style and passion for genuine connection. We believe photography should feel easy and joyful. We guide, support, and problem solve so you can relax and enjoy the experience.

Let’s create something unforgettable together.

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