Connor had a ring, a plan, and a Chicago getaway with Madeline. What neither of us had planned for was forty or fifty students joining me at the Honeycomb right before he was supposed to propose.


These two came from Houston, but Chicago already held a special place in Connor’s heart. With family roots in the Midwest and a serious love for Chicago sports, he wanted to give Madeline her own reason to love the city. They’d celebrated a Bears win at the game on Sunday, and he had an even better surprise planned for Monday morning!


Connor and Madeline met almost three years ago while visiting his best friend and her cousin near Texas State. It wasn’t a setup—they just happened to be there the same weekend! They hit it off, exchanged numbers, and a pizza-and-wine date followed. During our planning call, I loved hearing how much Connor appreciated having Madeline beside him through college and starting his career. He was so excited to ask her to marry him, and he’d taken her wish for a small, personal proposal to heart.


We had been planning for weeks, so I arrived early at the Lincoln Park Honeycomb to scout our spot. When I saw a bus unloading students, I had a passing thought: Hopefully they’re not headed this way. Sure enough, they joined me under the pavilion. Then I overheard the teachers explain that everyone would return at 10:50, with another group arriving at 11:00—our proposal time. Oh, goodness.


I texted Connor that we needed to pivot, found another pretty spot, and sent him a pin along with a photo featuring my very impressive finger-drawn stick figure showing him where to stand. Listen, whatever gets the job done.  But while he and Madeline were in their Uber, the students headed out to explore, leaving the Honeycomb empty. I sent one more message: if they could come straight over instead of taking their planned walk first, we could still do this exactly where we’d hoped.


And Connor made it happen! He brought Madeline to the Honeycomb, got down on one knee, and asked her to marry him. After all our quick texting and backup planning, they got their moment in the very spot we’d chosen. It was absolutely perfect.


Afterward, we got to slow down, take their first portraits as an engaged couple, and spend some time getting to know each other. That was my favorite part! Connor and Madeline were so much fun, and I loved being there to capture this little piece of their Chicago trip.


Connor and Madeline, thank you for letting me be part of such a special morning! You two are beautiful inside and out, and I’m so glad our paths crossed. From planning the surprise to celebrating with you afterward, this was such a joy! Now grab a blanket and snuggle up, your sneak peek is live!

Couple stands under a stunning wooden arch pavilion in a lush park with city skyline in the background.
Man kneeling on one knee proposing to woman outdoors on wooden deck with lush greenery and city skyline behind.
Man proposes on one knee to woman in park with city skyline backdrop.
Man proposes on one knee to surprised woman on wooden deck in park with city skyline backdrop.
Couple sharing a romantic kiss on an outdoor deck surrounded by lush greenery and a city skyline backdrop.
Couple sharing a romantic kiss on a wooden deck with Chicago skyline and lush greenery in the background.
Elegant marquise cut solitaire diamond engagement ring displayed on blue textured surface with silver band.
Couple embracing under a stunning orange wooden arch structure in a park with city skyline views.
Happy couple posing together under wooden arch structure with city skyline visible in background during engagement photos.
Couple embracing and about to kiss outdoors near an orange architectural structure with city skyline in background.
Couple sharing a romantic moment under a wooden arch structure in a park, man in navy blazer, woman in beige jacket.
Smiling couple embracing outdoors, woman in feather-trimmed jacket and man in grey sweater with city views behind.
Couple sharing a kiss while showing off engagement ring under orange arch in Chicago's Millennium Park.
Happy couple embracing under orange arch structure in Chicago park, woman showing engagement ring, city skyline in background.
Man lifting woman in a joyful embrace under a stunning orange wooden arch structure in Chicago park.
Couple dancing under an orange wooden arch pavilion in a sunny park with city skyline in the background.
Black and white photo of a couple sharing a playful, romantic dip and kiss outdoors.
Couple embraces inside wooden lattice structure, man kisses womans cheek.
Happy couple embracing inside a decorative wooden lattice arch structure in a sunny park setting.
Black and white photo of a romantic couple about to kiss, woman showing off diamond engagement ring.
Stunning wooden lattice pavilion with organic honeycomb design on a deck, surrounded by lush green trees.
Couple embracing by Lake Michigan with Chicago skyline and John Hancock Center in background on sunny day.
Couple embracing on a park path surrounded by autumn yellow trees with a city skyline in the background.
Couple holding hands and walking along Chicago lakefront path with city skyline and turquoise water in background.
Couple embracing and smiling on Chicago lakefront with city skyline and John Hancock Center in background.
Happy couple embracing and laughing by Lake Michigan with Chicago skyline in background.
Close-up of couple holding pinky fingers together with sparkling water and city skyline softly blurred behind them.
Soft-focus black and white photo of couple kissing with iconic Chicago Willis Tower in the background.
Happy couple walking hand in hand along a lakeside path with the Chicago skyline visible in the distance.
A joyful couple embraces on a lakeside promenade with a city skyline in the background on a sunny day.
Couple sharing a romantic moment by the waterfront, man lifting woman with Chicago skyline in the background.
Happy couple sharing a piggyback ride on a sunny beach with city skyline, woman holding an American flag cup.
A couple holds hands walking on a sandy beach with calm blue ocean waters and clear sky in the background.
A couple embraces on a sunny beach, the man in a gray sweater and woman in a beige fur-trimmed jacket.
Close-up of couple holding hands showing diamond engagement ring.
A happy couple embraces on a beach, with the woman kissing the smiling man on the cheek while showing an engagement ring.
Couple embracing on a sandy beach, man wearing a Polo Jeans Co. American flag sweater, woman in a beige fur-trim jacket.
Romantic couple kissing on a serene sandy beach under a clear blue sky.
Couple embraces on beach, man wearing Polo Ralph Lauren American flag sweater.
Joyful couple on a sandy beach, man lifting woman in the air while she laughs, both dressed in casual coastal outfits.

Congratulations again, you two! Houston, they’re coming home engaged!

Thanks for reading,

Handwritten signature reading xoxo Cassie in elegant cursive script on a white background.