The most common question we received in college was "when are you getting married?" Sean always told them, and Gillian, that he had to graduate, get a job, and pay off his debt before they could get engaged. Well, two years after graduation, the time had come, but Gillian is not a girl you can just ask to marry you - she deserves something special (and yes, this is Sean writing).

At some point in college, Gillian had noted an engagement ring she liked while reading one of her fashion magazines. Sean, who is always paying attention and never forgets anything (obviously still Sean writing), remembered this when he secretly began shopping for an engagement ring in January of 2005. Finding out Gillian's ring size by a process that still remains secret, Sean ordered the ring and began putting together a special occasion at which to present it.

Without Gillian's knowledge, Sean asked her boss for a couple days off for her (thanks, Joy!) and planned a long weekend trip to Boston, the city in which they had their first date back in the spring of 1999. On a Thursday morning after a long night at the Ivy (Mike Pezzicola, Proprietor and Chief Imbiber), Gillian woke up panicked, telling Sean that he was late for work. At this point it was difficult to keep the entire thing a secret, so Sean told Gillian to pack for a surprise trip.

Once they reached Boston, Sean had to work quickly, knowing that many of Gillian's friends, and more dangerously, her two sisters, knew that a plan was underfoot. As they walked through Cambridge looking for a place to find dinner, they got "lost" and serendipitously arrived at the same restaurant at which they had their first date. After dinner they took a walk over the Longfellow Bridge, which they had also done on their first date. Sean stopped at the first tower and began talking about their time together and their futures.

He could see at this point that Gillian expected him to propose, so he quickly turned around and kept walking towards Boston, claiming he was thirsty and could get a drink at the drug store at the end of the bridge. As Gillian tells it, at this point she was cursing under her breath and shaking her fists at the sky. But Sean couldn't let it go (he's not that mean), so he stopped at the second tower, got down on one knee, and proposed. Before he could even show her the ring, Gillian was crying and screaming yes (a testament to her potential mental instability). They continued across the bridge, an engaged couple, and the first person to witness their union was the cashier at Walgreens.