Robert and Savannah are high school sweethearts, who are now both in the Navy. So it was fitting when Robert decided to propose to Savannah at Chicago’s iconic Navy Pier. What was unique about this proposal, however, was the way he asked.

I had arrived earlier and was waiting inside at Faces in Focus Caricatures where the caricature artist was also awaiting the couple’s arrival. Robert had planned that they would stop by the booth for a caricature, and when it was finished it would be of Robert proposing to Savannah. Savannah, meanwhile, would have no idea of what was being drawn!

Luckily for me, there was a crowd of people watching the caricature artists, so I didn’t stick out like a sore thumb waiting to take photos of the proposal. The artist placed a sign by her drawing letting spectators know not to talk about the surprise, and we all stood and watched as shapes, colors, and Robert’s proposal came to life.

About a half hour later, the moment of the big reveal arrived. The artist picked up the drawing and showed it to Robert and Savannah. Everyone who saw the caricature being drawn, held their breath in anticipation. A big, surprised smile appeared on Savannah’s face as she registered what she was seeing. At that moment, Robert got down on one knee and pulled out the ring.

She said YES! And the crowd erupted in cheers and excited chatter. It was perfect!

After the proposal, we went outside to get some photos around the Ferris Wheel and other rides that were beautifully lit up at night. Congratulations, Robert and Savannah!

Hand lettering by the wonderful Dancing Ink Calligraphy.

If you liked this post, feel free to comment below! Interested in booking a proposal or engagement session? Contact me and we’ll start planning!