It was the coldest day Washington DC has seen in the last 5 years. The temperature was 10 degrees Fahrenheit and Matt decided to make it easy for Paige and pick a place in Georgetown, not far from her Glover Park apartment. Matt arrived early to the Sovereign and sat at the bar, drinking a couple tequilas to calm his nerves. Meanwhile, Paige was looking for an excuse to skip the date and calling mutual friends to try and find a believable story. Fortunately, a couple of Bucknell friends, some who met Matt in the Bahamas years before, convinced Paige to get to that date. Paige and Matt bonded immediately over their shared connection to Connecticut, having Dads who are doctors, and the strange amount of Bucknell people Matt knew. After sharing an awkward first date hug, the two went their separate ways, oblivious to the fact that this would be the start of something special.
Matt had the ring securely hidden in his hamper for 4 months, patiently waiting for a trip to Martha's Vineyard. MVY is Paige's happy place and where her and Matt's relationship grew each year. Matt knew this was the place he had to propose. The only possibility was the Brennan annual family vacation. Matt woke up at 6AM Monday morning, which Paige thought was odd because she was always the first one up. Filled with nerves, Matt provided Paige's sisters with their "plans" for the night. Lisa concocted her own plan, which was even a surprise to Matt. Matt and Paige were on their own for the evening, so Matt asked if Paige wanted to go have some wine by the Edgartown Lighthouse, one of their favorite spots on the island. Morgan's fiancé, Zak, snuck out of the house in full disguise to stake out a photography position. After Paige and Matt drank a little rose, Matt asked Paige if she wanted to feel the water (he didn't think about the fact that they would be sitting and he needed her on her feet). With the Lighthouse as their backdrop, Matt asked Paige if she would spend the rest of her life with him. Paige's family abandoned their fake plans and were waiting patiently at the Harbor View Hotel for some celebratory drinks.