Jared and Ashley first crossed paths at a friend’s gathering. A few weeks later, fate brought Jared to the salon where Ashley worked, and she became his stylist. Although they recognized each other from the party, they kept it to themselves and bonded over travel aspirations and adrenaline-inducing activities like skydiving. After their encounter, Jared reached out to their mutual friend, Tony, to confirm Ashley's identity. Tony, who knew them both well, provided Ashley's contact information, sparking the beginning of their relationship. As they delved deeper into their connection, they unearthed a surprising twist: they had attended preschool together, a discovery made while flipping through old photographs.

Jared and Ashley journeyed to Niagara Falls, Ontario, eagerly anticipating Theo Von’s Comedy Show. Prior to the event, they planned to rendezvous with Tony and Shanece Ivey for lunch. Entering The Rainforest Café connected to their hotel, they searched in vain for their friends. A call revealed the mix-up: Tony and Shanece were at the Rainforest Café on the New York side of Niagara Falls, unable to cross the border. Disappointed, Jared struggled to conceal his frustration, leaving Ashley puzzled until a stranger at the falls offered to capture a momentous photo of the couple: the proposal. It was later revealed that Tony was meant to be their videographer, but failed to go to the correct country..