Our Story

It all began in 2017, when fate—and a unisex bathroom line—brought us together in the most unexpected place: a bar called Mezzo’s in Middletown, Connecticut. Ryan had just finished his super senior year at the University of Texas, and Caroline was finally celebrating the end of her grueling 4 a.m. weekend shift at ESPN.

Ryan showed up that night in his best Hawaiian shirt, while Caroline, thrilled to enjoy one of her first weekends off, was a few drinks in and feeling bold. Standing in line for the bathroom, she turned to Ryan and said, “Digging the shirt,” complete with finger guns. Flattered by the compliment, Ryan struck up a conversation, learned her name and where she worked, then let her cut ahead in line.

When Ryan emerged from the bathroom, Caroline was gone, and his friends were ready to leave. But something told him not to let her slip away. He found her on the dance floor, asked for her number, and later that night, sent what he thought was a clever text offering to take her out in exchange for insider knowledge on Stephen A. Smith.

What started as casual dating quickly took a surprising turn. A few months later, while Caroline was visiting her grandmother, she mentioned how some of her belongings had been stolen during a move. Her grandmother called it a “blessing in disguise” and began talking about her own friend, a woman who had recently lost her husband and was moving all of her belongings into her daughter’s home in Milford.

Curious, Caroline asked, “Wait, is this the Cuppernull family?” Her grandmother replied, “No, no, it’s the Kraffmiller family.” Then, as she continued sharing details, she showed Caroline the funeral pamphlet—and there, listed among the family names, were Ryan and his siblings. As it turns out, “Kraffmiller” was Mrs. Cuppernull’s maiden name, and their grandmothers had been good friends for years, meeting for breakfast together every Monday.

Ryan came home that same day to his grandmother insisting, “You have something to tell me about!” And just like that, Caroline was officially invited to meet the family.

The rest, as they say, is history.