Like all great modern love stories, Anna and Connor’s began on Hinge. Connor broke the ice with a clever line complimenting one of Anna’s photos — highlighting a makeup look for an EDM festival that she had spent much too long perfecting (and yes, it worked). At the time, Anna was about to leave for a week to visit her grandparents in Ohio, so Connor simply asked when she’d be back in Chicago and told her he’d text her then to set up a time to meet for drinks. Anna, fully convinced he was bluffing, told him she’d return the following Sunday. Much to her surprise, he texted her exactly when he said he would, the moment she returned to the city. Pleasantly surprised (and impressed), she agreed to the date. They had their first date at Eduardo’s in Old Town on St. Patrick’s Day 2022. A week later came date number two, and by the very next night they decided they didn’t want to stop seeing each other — so they didn’t. They’ve been inseparable ever since, and by late April 2022, they made it official. In September 2023, they moved in together, and Connor quickly became the very best dog dad to Anna’s pup, Ziggy — fully embracing his boundless puppy energy and all the chaos that comes with it. Two years later, on September 13, 2025, Connor somehow managed to pull off the surprise of a lifetime. He told Anna they were going to a fundraiser for his cousin’s work, but instead, with the Chicago skyline as the backdrop, he got down on one knee and asked her to marry him (the exact moment pictured below). To make it even more meaningful, their families were waiting nearby to surprise them, and the night ended with a celebration surrounded by so many of their favorite people. It was the best day of their lives — so far. Over the past four years, they’ve cheered on the Cubs at Wrigley Field, eaten their way through Chicago’s restaurants, found their favorite dive bars, braved cold Chicago winters, danced at EDM shows and music festivals, spent long summer days at the lake, taken countless walks with Ziggy, and shared so many beautiful memories with the friends and family who mean the world to them. At the end of the day, their favorite thing has always been simply being together. As they often say, “I just want to hang out with my Bubby” — the endearing nickname they both use, even though neither of them quite remembers how it started. Anna and Connor (and Ziggy) feel incredibly lucky to celebrate their wedding in the city they love most, surrounded by the people they love most. Now, LET'S PARTY!