One Sunday in January 2020 at Our Lady of the Pillar church, Jimmy and Allie crossed paths. Jimmy, accompanied by his dad, received a nudge to ask Allie out upon learning she was single. Jimmy met Allie after church with introductions facilitated by his father.

Later that night, Jimmy took the initiative to connect with Allie on Facebook, asking her out for drinks. Allie agreed, providing her number. Their first date took them to Sqwires Restaurant, marking the beginning of their relationship.

In June 2023, Jimmy surprised Allie with a trip to St. Lucia, culminating in a challenging hike to the top of the Gros Piton Mountain. Despite doubts from Allie during the difficult ascent, a well-planned proposal unfolded at the peak, capturing a significant moment in their relationship.

Ironically, despite growing up within a mile of each other, attending the same parish and college, Jimmy and Allie never formally met until that day in 2020.