Gracie Cashman, the daughter of New York Yankees general manager Brian Cashman, was taken aback by a marriage proposal that was truly out of the park. Gracie, 26, answered “yes” after boyfriend proposed onstage in Chicago, with the couple’s families hiding in the opera boxes. In an exclusive conversation with Us Weekly, Gracie explains how her new fiancé pulled off the massive lie. “I knew his family was in town for his little sister’s birthday,” she told me. “He told me we were going to have brunch and dinner.
I figured we’d spend the weekend with his family, so I had no plans. He stated we needed to stop at a bakery to get a birthday cake before brunch. We didn’t stop at a bakery on the way there; instead, we headed to a theater I’d never been to before.”
Gracie said, “When we walked in, it was entirely vacant. The stage, everything. He led me to the stage, went down on one knee, and asked me to marry him. Stute chose the proposal’s site for a very special reason, recalling their time together at St. Luke’s School in New Canaan, Connecticut. “We met in high school doing Legally Blonde: The Musical, which is why he proposed on a stage,” Gracie told me. “I played Elle, and he played Warner. We started dating during my junior year of high school and his senior year.
We did break up near the end of college, but we got back together when we both went to Chicago.” She continued, “We weren’t very adept at breaking up anyway. We were pretty much constantly talking.”
Following the proposal, both families – including Gracie’s split parents and brother, Teddy – emerged and took photos with the newly engaged pair before the entire crew hopped into a trolley – “a very Chicago thing to do,” Gracie joked – loaded with Fireball shots. “We were laughing,” Gracie recalled, “because everyone on the trolley was like, ‘Oh my god, it’s 11 a.m., but should we do the Fireball shots?'” Definitely.'” Stute proposed to Gracie using her grandmother’s ring, Mary’s late mother. “She died when I was 2,” Gracie explained. “My mom had her engagement ring and she let my boyfriend use it.”
Of course, now the wedding preparation process begins. But Gracie, who presents The Story of My Number on The Gotham Sports App, has encouraged her friends and family to be patient while she plans the big day. “I think we’re going to have to pick a date pretty far in the future,” Gracie told me. “I think we’ll set a date in the winter.” I’ve always wanted a winter wedding. I believe that two years from now, in the winter, people will have enough time to figure it out.” In terms of location, Gracie stated that she has “always wanted to get married abroad” and has her sights set on a specific destination.
“I’ve always wanted to do Ireland,” she explained. “I haven’t been to Ireland in years, but my father is 100% Irish. My mother is nearly 50% Irish. So, I’m more than 75% Irish. We’re a fairly conventional Irish Catholic family in many aspects. I would want to do it there, but we’ll see.”
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