It's been 10 years since he's been back to Stars Hollow. Dean is 33 years old now and graduated from UCONN with a degree in Architecture. He's single and works for a small Architectural Firm based in Washington, DC. His father passed away and he's back in town to take care of family affairs and to arrange the funeral and help his mom for a while.
Dean and Clara were walking through the town reminiscing about old times. Things seemed to have stood still in this small town. The people look the same, maybe a little bit older, but the town still retained its quirky charm.
Dean and Clara made their way past Doose's Market where he used to work as a teenager, and then again in his young adulthood when he was going through some life changes. This town and its people had seen him through many phases of life. They saw him fall in love for the first time with the town princess Rory Gilmore. They saw him get his heart broken by her and struggle to work his way through it. In the same way the town watched Rory grow up and endure the hardships of life and love, they had also seen Dean flourish and flounder through life's trials.
After Dean's marriage to Lindsay failed, they had both struggled to come to terms with it. Though Dean's deep seeded love for Rory was the catalyst for the failure of this union, they both came to the realization that they had married too young, and for the wrong reason's. Lindsay wanted a fairy tale, and Dean wanted to ease the pain of losing Rory. Eventually the two continued on with their lives letting time and distance deaden the pains they both felt.
Lindsay ended up married to a very nice young man from another small town and had moved there a few years later. She still lives there in her perfect little house with a picket fence. It was everything she had always wanted. Dean made his way back to school and threw himself into his studies and after graduating threw himself into his work. They kept in touch sending Christmas cards and the occasional email. Dean lost touch with Rory after a while… it was just too painful.
Clara and Dean passed the gazebo and Dean stopped for a moment and let his mind take him back…. It was that spot. They had many conversations, many moments of contentment right there. He chuckled slightly to himself. Clara noticed her brothers grin and knew that he was thinking of her.
Clara had known all along that Rory was always the Stella to Dean's Stanley. Even as a young child her heart broke for him. It seemed no matter how hard he tried, it just wasn't going to work. Clara had seen her brother cry and try to hide the pain and confusion he felt. After all this time her big strong brother protected that small ember in his heart for Rory. To Clara, Dean was always the protector, but with Rory it was though he needed to have his heart protected.
As they approached the Church building Dean kept his eyes lowered. This was the place where he made the decision to change his life. Several years ago he would have said that this was the place where he made the worst decision of his life, but with age comes a bit of wisdom. He had come to terms with his past and the decisions he had made. Dean knew and accepted that what had happened was part of who he was now. He knows that he is just a compilation of all his past experiences… some were just easier than others, but each helped him grow.
Clara sensed her brother's demeanor change. She knew all too well what this building represented to him. Once inside they spoke to Reverend Skinner and made the arrangements for their father's memorial. When they were done Clara went back to their parents house to be with their mother and Dean continued walking through town. He passed by the ball field were he used to play softball on Sunday afternoons. He walked by the High School and he stopped by The Tree.
The Tree. This was where he first saw her. He sat under the shade of the tree and once again let his mind wander as he picked at the grass beneath him…
She would sit there for hours reading, oblivious to what was going on around her. She would lose herself in her books. It was one of the qualities he found so fascinating about her. She wasn't like all the other girls who were so preoccupied with what was going on in their small little cliques. She was just Rory, no pretenses, no agenda, just a girl with eyes that seemed to see through you to his soul.
They were young and it was many years ago, but he couldn't help but remember what he felt when he was around her. She saw things in him that other people didn't see. She challenged him to read things and try things that would never had occurred to him to attempt. With her he read Russian novels, learned to waltz, ate candy till he was sick, and became interested in seeing the world. She was the only one that believed he could go to a 4 year college and succeed. Rory wasn't one to settle. She would strive for the best and she pushed whoever was around her to do the same. He loved her and at that time it seemed like that love would never fail him. He got complacent, but the love didn't fail him… it just out grew him. He knew Rory needed to be surrounded by people with big dreams, big hopes, goals that seemed so far out of reach. He just wasn't ready for that. He wanted what he had with her and nothing more.
He knows now it would have been a mistake to stay that way. Where would he be now if she let him stagnate? He wouldn't be designing buildings that appear in books and magazines. He knew he would never have been able to make her happy if they stayed in that place where they were. They needed to grow… and it happened that they grew apart and took different paths. Such is life.
They day he saw her in her party dress and diamond tiara was the day he knew she was destined for something bigger than he could imagine. He just didn't believe that he was also destined for something big. Confidence was something Rory had not him. She had an unyielding confidence that drove her to achieve everything she set out to. He on the other hand was grateful for each time he didn't fail.
Now things are different. He had found his path in life. He was good at what he did and he loved it. He traveled the world, studied the ancient ruins, stayed in cities he had never dreamed of seeing. He wondered if she realized her dreams. Now that he thought about it, the big difference between them was that Rory knew at age 15 what her dreams were while Dean hadn't known he even had aspirations until he was pushed. Now he was an adult and he was driven to succeed. It always seemed quite ironic to him that he was always willing to be what Rory wanted him to be, and at the same time she was pushing him to be everything that he could be.
He was finally able to be happy that she always would have a small place in his heart. She would be the standard by which he measured everything. He just wishes that he would thank her. It would just be silly now, but he really felt he owed her that. After all, she knew it when everyone else couldn't see it. Dean had a future, a road to be traveled.
The weather grew chilly and Dean snapped out of his trans. He made his way back to his parents house to prepare for the memorial the next day.
Morning came and Clara and Dean were dressed and ready to head to the Church. His parents had become part of this quirky little town as well, and many of the townspeople came to pay their respects and give condolences to Dean and Clara. The service was subdued and many of Dean's father's friends and coworkers had many nice things to say about him. Dean was the last one to speak.
"I am not very good at public speaking. It's one of the things that I inherited from my father. My dad was a quiet man. He went about his business and took care of his family. He lived a quiet life and had great hopes for his children. He was the rock of our family. He kept us grounded and taught us the importance of family.
There are very few people who I can say believed that I would be something some day. One of them is an old friend who was wise beyond her years, the other my little sister, and then there was my dad. My dad taught me that being humble was part of being great. That great people didn't always have grandeur, but they always had respect.
I respect my old man. He was the most honest, hardworking, caring, and forgiving man I have ever known. I owe him for teaching me to have my feet firmly planted on the ground. For teaching me that mistakes aren't what people remember you by… it's what you do after you make a mistake that leaves a mark.
I am who I am today because of my father. I love you dad."
With that, Dean looked into the crowd and their eyes met…..