In summer 2023, Rita went to The Avanti Group’s annual Summer Serata at Gibsons Italia, a rooftop party for Chicago’s young Italian American community. She’d been part of the group for two years, mostly to make new friends (and maybe meet a nice Italian guy), but had pretty much given up on that part. That night, Jack and his friend Ben happened to snag the last two tickets to the sold-out event. Before heading out, Jack told Ben he “had a feeling he’d meet his wife tonight.” Rita got there early and was waiting outside when it suddenly started raining, forcing her to head inside & right into Jack’s path. Inside, the two guys immediately started talking to her, whether she liked it or not. When Jack accidentally turned down the crab claws (Rita’s favorite), he quickly made it right by chasing down the waiter to bring her some. They spent the rest of the night dancing, laughing, and have been inseparable ever since