Mac has always been a planner. However, just about everything with the proposal did not go quite as expected… Mac had the perfect engagement ring crafted in California. He had it all planned out - he would have the ring delivered to his sister's house to avoid Olivia's suspicion. He tracked the package and texted immediately when he saw the delivery notification. “Did you get it?” He asked his sister. "No?", was the response. It had been delivered to the wrong house. After a furious phone call to an unfortunate FedEx employee and a short door to door search, the ring was found. Unfortunately, the problems did not stop there. Mac was scheduling the perfect day to propose to Olivia. He had reserved an evening at the beautiful Nasher Sculpture Museum and hired a photographer. Yet, the world had other plans… Less than a week before the planned date, the event coordinator notified that she would have to cancel as she had come down with COVID. Mac scrambled to pivot, booking a lovely rooftop bar to lure Olivia into a drink before dinner at their favorite restaurant. Upon reaching the rooftop with a space marked "Private Event", Mac encouraged Olivia to take some pictures overlooking the Dallas skyline. Unsuspecting Olivia, concerned about encroaching on someone's space, cautioned her soon-to-be Fiancé, but Mac knew better. As the moment neared and the cold January air began to take a toll, Mac took a moment to grab Olivia's attention and ask if she would spend forever with him.