Have you ever brought a chaperone to your first date? Maybe you’ll think it’s a sign of good luck after hearing this story. When Max asked Janna out to pizza, she decided it’d be a good idea to bring her roommate along! Although at first Max was a little skeptical, Janna was more comfortable around her. Ultimately they went on a second date, and many more, sans chaperone. And now they’re engaged!

When Janna first contacted me, she told me about how much the two of them have spending time outdoors. I immediately knew we’d get along well! It was fitting that Max proposed on a group trip to the Northern Woods of Wisconsin. His original plan was to propose using one of their favorite board games – Sorry! But Janna forgot the sorry board at home when they left for their trip! Max had to improvise. Thankfully their cabin was nestled against a lake with a beautiful pier. All of their friends were in on the secret so when Max walked out alone to the pier, everyone else went inside to let them have their moment.

At first, Janna didn’t know where Max was. She was looking for him, but couldn’t find where he went. After waiting alone at the end of the pier for awhile, Max sent Janna a message to come to the pier. She was worried. She thought something was wrong. Why was Max waiting at the end of the pier alone? She cautiously walked out to the pier, preparing herself for the worst. When she reached the end of the pier, Max looked extremely nervous which made her even more worried! Thankfully, it was instead the best news as he dropped to one knee and asked her to marry him! Afterwards, they spent the rest of the evening celebrating with friends.

Their engagement session started out with a light drizzle which gave way to a nice sunset. I actually love when a storm passes through because the storm clouds look so cool over the lake as the sun starts to set. They brought their dog, Ralphie, along too. He is the cutest little dog! When I asked if Janna and Max were feeling adventurous enough to end their session in the water, they didn’t hesitate. I’m so glad they were up for anything because those are my favorite photos from their session!

Janna and Max are tying the knot next summer in the North Woods of Wisconsin. It’ll be a similar setting to their engagement at a lodge nestled up against a lake. I can’t wait to photograph their wedding! In the meantime, enjoy a few of my favorites from their engagement session.

Hair and Makeup: Tiffany Tallinger

Florals: Belle Fiori Milwaukee