Romance by the Lake: The Engagement Session of Anna & Scott

Sometimes, the best love stories begin with a plan that doesn’t quite go as expected—and for Anna, that couldn’t be more true. “Scott and I met on Hinge in January of 2022,” she shares. “My New Year’s resolution was to go on as many first dates as I could—turns out that was one resolution I wasn’t meant to keep!” What started as just another first date quickly became something much more meaningful, proving that the right person can change everything in an instant!

When it came time to propose, Scott chose one of Chicago’s most iconic landmarks, but made sure the moment was anything but predictable. “Scott proposed in front of Buckingham Fountain in Chicago,” Anna says. “We have had an ongoing inside joke about that fountain since we moved here, so I think I would’ve seen the proposal coming—but he had me convinced that we were meeting a friend of his to go on a ‘gangsters and ghouls’ walking tour.” Completely unsuspecting, Anna was scanning the crowd for someone else entirely when the moment unfolded in the most unexpected way. “My mom walked up and handed over the ring box to Scott, saying, ‘Excuse me, I think you dropped this!’” Anna recalls. “I was so completely surprised, I stepped backwards, rolled my ankle and almost fell.” Luckily, Scott was right there! “Scott held my hand and, with the most romantic speech, proposed!” It was a perfect mix of heartfelt, personal, and just a little bit unforgettable chaos—the kind of moment they’ll laugh about forever.

Scott took on the task of choosing the ring entirely on his own—and the result couldn’t have been more perfect! “My ring is absolutely stunning,” Anna says. “It is a round brilliant cut diamond on an intricate yellow gold band, with delicate vines and leaves along the band and setting.” Though he handled the design, Scott did have one final checkpoint. “He did ask my sister for final approval!” Anna adds. What makes the ring truly special, though, is how well it reflects Anna. “My favorite part is the detailing—it’s unique, and it matches my style perfectly.”

For their engagement session, Anna and Scott chose a location that felt deeply connected to their relationship. “We picked Museum Campus in Chicago because we knew it had all our favorite parts of the city in one location—a view of the skyline, a view of the lake and still tons of greenery,” Anna shares. “We’d done so many dates there, so it felt right!” The setting offered the perfect blend of natural beauty and iconic city views, capturing the essence of their life together in Chicago.

Choosing the right photographer was an easy decision after seeing her work firsthand. “We met Abby when she photographed my twin brother’s wedding in June of 2025!” Anna says. “We were obsessed with the style of the gallery—she captured the magic of the day for my brother, so we knew we could trust her to capture our day, too.” That trust paid off, resulting in a gallery that beautifully reflects both the romance and reality of their relationship.

When it comes to their wedding, Anna and Scott are focused on something deeper than just the day itself. “We knew we wanted to plan a marriage, not just a wedding,” Anna shares. “And we knew we wanted our wedding to celebrate not just us, but our friends and family who helped us get here.” Their vision reflects that intention, blending meaning with creativity. “We’re planning a very fun, low-stress, fantasy-inspired ceremony and reception, and we’re so excited to bring our vision to life!”

Now well into their engagement, the couple is embracing the planning process together. “We’re just past the halfway point of our engagement, and wedding planning is in full swing!” Anna says. “We’re having a lot of fun with it.” Their approach has helped keep things balanced and enjoyable. “Sticking to checklists and spreading out the decision making has helped us lighten the load.” And as they continue planning a celebration rooted in love, creativity and connection, one thing is certain—their story is just getting started!

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