A modern couple, Anali and Rory met in a modern way! She was intrigued by the photo of him playing soccer, only to find out it was an Irish sport called hurling. He liked her smile and asked her to dinner that night. Rory talked a lot about his family, his Irish heritage, and cross country. Anali listened and laughed, charmed by his ease and how much they had in common, including: their faith, their schooling, and their love and undying devotion to family. They proceeded to close the place down that night.

Anali and Rory attended mass that Sunday, as he was headed to San Jose for the holidays. They texted and talked, even learning how to use the Marco Polo app to stay in touch. They kept communicating daily while together or apart, in one form or another, during good times and bad. Learning how to talk, when to speak, and when to listen are all important communication strategies. In that spirit, they no longer use Marco Polo! Six months into their whirlwind romance, Anali met Rory’s boys Chris and Casey, who were in middle and high school at the time. Rory met Anali’s family the following Thanksgiving. "Finally! Someone to get that woman a glass of ice water before bed," said Madeleine, Anali's daughter. Needless to say, her family liked him instantly because he made their mom happy.

Six years later, in 2024, during the exchange of gifts in front of the O’Flaherty family Christmas tree in Saratoga, Rory (in his track suit and hoodie) went on one knee and proposed to Anali amid the whooping and hollering of the entire O’Flaherty clan. Anali was excited to say yes, surrounded by the family who made her feel so welcomed and included. Maire, Rory’s mom, asked, “What’s happening?!” Rory wanted Anali to choose her perfect engagement ring, so the very next day Niamh (Rory’s sister), Niamh’s daughter Christina, and Brendan’s wife Jeanette promptly swooped her out to San Francisco to visit the family's favorite jeweler. She loved picking the perfect ring alongside the keen eyes of her future sisters and niece. Needless to say, Maire approved of the events that day. And that was that.