On one unforgettable day, John took a leap and "liked" a profile on Hinge—a woman named Skylar. Assuming this would be like any other match, he proceeded to overshare his entire life story, leaving poor Skylar blinking at her screen, completely blindsided. But despite John's digital monologue, Skylar felt something and decided to take a chance on this guy who seemed to have zero filter. John, however, wasn’t quite ready to wait until their official date. So, in what can only be described as a bold (some might say borderline stalker-ish) move, he decided on a pre-meet: he would "accidentally" bump into her at her workplace... Olive Garden. When they finally sat down together, John couldn’t stop staring at her. Something just clicked, and as they bonded over her impeccable taste in music, he knew she was something special. By the end of the night, as Skylar walked him to the door, John was brimming with confidence. Without missing a beat, he reached over, pulled her mask down, and went in for the kiss—a heart-stopping first kiss that neither would ever forget. That’s when history took over, pulling them from that Olive Garden doorway into a future they were both more than ready to jump into.

The day John proposed was nothing short of chaos and romance wrapped into one. Skylar was completely unsuspecting. They’d just driven eight long hours from Maryland with all five kids in tow (Levi, Nolan, Lucca, Maggie, & Violet) , and John had been secretly conspiring with her sister, Savhanna the whole time. While they were making their way back to Rhode Island, the two had everything set up—roses, candles, the works. As they finally pulled up at home, Skylar, in her usual style, went straight for the front door to grab a stack of packages. John's heart raced. Was the plan about to fall apart? But, just in time, she circled back to the side door. Relieved, he took the packages from her—playing it cool until her eyes narrowed just a bit. Skylar could feel something was up. The moment she stepped inside, she froze. Everywhere she looked, there were roses, hundreds of them, filling the room in a sea of red. Candles flickered softly around the space, casting a warm glow. Stunned, she turned to see John dropping to one knee, looking up at her with a hopeful smile. Before he even finished the question, Skylar was beaming, “Yes!” Now, they can’t wait to celebrate this beautiful new chapter with all of you