An Associate Engagement by Cassie at Lincoln Park & North Avenue Beach- Kayle & Connor

Earlier this week, Cassie met up with Kayle & Connor for an evening exploring two of my favorite Chicago locations… Lincoln Park and North Avenue Beach. Between the city skyline, the lakefront, and so many genuine laughs, these two made the entire session feel effortless.

Their story began five years ago after matching on Bumble. What started as a July meeting eventually turned into dating that December, and today they’re planning forever together. Connor completely surprised Kayle with a proposal at Apple Holler, a special apple orchard her family visited growing up. Even though he kept insisting he was “still working on it,” he had quietly planned every detail… including a photographer to capture the moment!

Kayle & Connor, thank you so much for having us! Cassie had such a wonderful time getting to know you both, and we are so excited to be part of this season of your lives.

Now, grab a blanket and snuggle up. Your sneak peek is live!

Kayle & Connor, thank you again for hanging with Cassie for a fun evening together! We loved getting to know you both and already can’t wait to celebrate alongside you on your wedding day.

Much Love,