Tim and Fiona met in the emergency room at Lower Manhattan Hospital, while at work. Tim noticed Fiona right away and soon, he was bringing all of his patients to her hospital, hoping to run into her. Gradually, Tim began spending more and more time at the hospital after dropping off his patients, chatting with Fiona and getting to know her.

Tim and Fiona both went to the LMH Holiday Party, where he decided it was finally time to ask her out (four months later). He even had his Aunt Mena help him pick out a new suit for the occasion. Being that their schedules are a little hectic, they decided on Christmas Day after work as their first date. Tim arrived at the hospital to pick Fiona up with a beautiful bouquet of flowers and opened the car door for her (which he still does now, every time). Fiona knew by the end of the night that he was The One. Tim knew she was The One even before that.

Just short of a year into their relationship, their families gathered at their house for a Christmas Dinner. Fiona was adamant that the dinner be casual with a theme of Christmas Pajamas, though Tim tried to convince her otherwise. Adrian handed Fiona a wrapped present from Tim, which turned out to be a Lenox ornament of a ring in a box saying "Better Together." Confused, Fiona turned to Tim, who was down on one knee, asking her to marry him. Completely shocked, gnome Christmas Pajamas and all, she said yes.