Shaila and Jeremy at Lost Lake

Our Story

Jeremy grew up in Madison, Wisconsin and moved to Chicago, Illinois right after receiving his double bachelor degrees from UW Stevens Point in 2006.

Shaila moved around a lot growing up, living in ten different cities (she loves cities), but she had always wanted to live in Chicago. When she finally made the move in 2016, she was excited to make new friends and take on everything the city had to offer.

Jeremy and Shaila met while working for the digital team at a personal loan company. It was Shaila’s first job in Chicago and Jeremy’s fourth.

They became friends when they realized they shared an interest in the tabletop game Dungeons and Dragons, with Jeremy asking Shaila to find a place where he could finally play. After finding and playing a local Adventurer’s League game at their now favorite game store, Dice Dojo, Shaila started running her own weekly game. Pretty soon they were hanging out regularly for D&D, board games, movies, and long late night conversations.

After one of those late night convos Jeremy finally got the nerve to let Shaila know he was interested in being more than just friends, then promptly left town with his family for a week. They still can’t agree if their anniversary falls on the night of the movie they saw before he left, or the one when he returned.

The next three years were a whirlwind of travel, 8 board game conventions, 6 camping trips, 4 national parks, 24 tiki bars, 81 escape rooms, and 1 lockdown for a global pandemic.

In the middle of that pandemic Jeremy gathered a few of their close friends for a game of D&D in search of a magical ring. That night ended with the party winning said ring in a race to the top of a mountain and Jeremy down on one knee proposing.