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It all began thanks to their favorite matchmakers—twins Ashley and Brady—who decided Matthew and Natalie needed to meet. So they organized a not-so-undercover setup: happy hour at Bear Ridge Pizza (LMNO) in Cohasset, followed by a potluck and campfire at the St. Germain’s house. Everyone there was a married couple… except for Matthew and Natalie— Subtle, right? Not only were their friends fully invested in the setup, but their friend's kids were too—cheering them on from the sidelines with the kind of hopeful giggle energy only tiny matchmakers can bring. Sparks flew, laughs were shared, and just when things were going well—Poof! Matthew pulled an Irish goodbye. Natalie wasn’t sure if she’d see him again, but decided to be bold and sent him her number… with one tiny problem: she accidentally mixed up a digit. So when she didn’t hear from him, she figured he wasn’t interested. Meanwhile, Matthew had texted her right away—and when she never replied, he tracked her down on social media to see if she’d gotten his message. A few DMs later, they were officially connected—and the rest is history. Matthew quickly gained fans—of both himself and his mustache. Thanks to Natalie’s niece and nephew, he was promptly nicknamed 'Mustache Matt,' and he’s been winning hearts ever since.

While vacationing in Cabo with the Newton crew, Matthew saw the perfect opportunity to propose. The group set sail for a sunny boat adventure filled with snorkeling, ocean breezes, whale watching, and... Matthew being suspiciously quiet. Natalie just assumed he was feeling a little seasick—what she didn’t know was that he had a diamond ring burning a hole in his pocket the entire time. After a swim, Matthew suggested they take a picture at the bow of the sailboat—his grand vision? A romantic Titanic pose. Natalie was not exactly sold on the idea, but Matthew persisted and asked her to face the ocean. As she stood there, reluctant and very confused, Matthew handed Natalie’s brother-in-law a phone to snap the shot—despite there being a literal professional photographer on the boat. Then came the moment: “Okay, you can turn around now.” When Natalie turned, there was Matthew—down on one knee, ring in hand, and shaking like a leaf in the sea breeze. Shocked, thrilled, and now fully understanding why he’d been acting weird, she said YES!