Greg was at a Dooley Noted party and so was Gillian's best friend, Rachel, who asked Gillian to come pick her up in the middle of the night. When Gillian arrived in her PJs, Rachel said, "This is Greg, he lives next to us so we're taking him home." Gillian and Greg stayed up all night talking about musical instruments and life, and the rest is history.

Gillian knew she loved Greg at a Waffle House after one of Greg's performances. Between his mesmerizing musicianship and uncouth humor, she was hooked. Greg knew he loved Gillian when they took a 5 day cruise together and back on dry land he realized he wasn't tired of her. OK - you know Greg, it was actually much more gradual. But on the day he decided to tell her how he felt, he took her to Chow Baby but forgot his wallet. To make it up to her, he built her a fort and confessed his love.

Greg set up a scavenger hunt for Gillian taking her to their favorite places in NYC. The tour finally led her home, where he had her favorite dinner and a ticket to the Empire State Building waiting. When she got there, all the doormen and attendants treated her like a princess letting her skip lines, take special elevators, and telling her she was a V.I.P. (yes, Greg told them to do that - and yes, Gillian thought she was just having a good hair day). When she got to the top, Gillian walked around the observatory but didn't see Greg. Just when she was about to give up, they spotted each other through the window and Gillian ran to Greg! On the 102nd floor where they were nearly alone because it was so late, Greg got down on one knee and popped the question. Gillian, of course, said yes!