I don't own The Crazy Ones and never will. No copyright infringement intended.

Simon woke up on the morning of Sydney and Andrew's wedding day ready to cry. His little girl was definitely growing up and while excited for her, he was a little sad. He still (barely) remembered the day she was born and now everything was about to change forever. He loved Andrew, however, and thought those two were a good fit. Plus, everyone who knew them saw this coming (except for the couple themselves until Lauren had snapped two years ago and meddled). Andrew managed to get Sydney to calm down and stop being working so much when she got a little too into it. In turn, she got him to loosen up. They complemented each other pretty well.

"You look beautiful," Simon told his daughter that afternoon as they prepared to walk down the aisle.

"You really think so?" Sydney loved her dress, but she was worried no one else would like it.

He nodded. "Let's get the show on the road. I love you."

She beamed at him. "I love you too, Dad." Sydney linked their arms together and nervously took a deep breath. When they reached the end of the aisle, Simon had a moment and refused to let go of her arm. "Dad, let go."

"I don't want to," Simon mumbled.

She stared at him until he let go. "Thank you."

"You're welcome." A few seconds later, after he said what he was required to, Simon sat down in his chair. Best man Zach made fun of him later for his inability to let go, but Simon showed him on the dance floor during the reception. He shed a lot of tears as Sydney and Andrew exchanged vows and kissed for the first time as husband and wife.

"So, are you changing your name?" Lauren questioned later once the two took a break from making the requisite rounds.

Sydney glared at her. "Didn't we talk about this multiple times before?" She didn't want to get into this again, especially not on her wedding day.

"I forgot?" she tried.

"She's keeping her maiden name professionally, but going by Sydney Roberts-Keannelly otherwise." Andrew grabbed his new wife's hand and kissed it.

She melted. "You have to stop making me cry today. The waterproof mascara really sucks for some reason." Sydney really didn't mind all that much, however. She could be sappy today if she wanted to be. It was her right as the bride.

"Sorry." He really wasn't though. Andrew kissed her again and then walked away to talk to a family member. Sydney followed her husband.

They were both a little embarrassed when Simon started singing karaoke despite the fact they hired a DJ, but everyone (excluding Andrew's extended family – they didn't know him and were thus a tiny bit terrified) waved it off as normal Simon behavior. Besides, it was entertaining and others ended up joining in. Sydney even got in on it at one point.

Later that night, once mostly everyone had gone home, the few remaining people sat around talking (and drinking, because it was an open bar) about random shit.

"It's been a long day." Sydney kicked her shoes off (her feet were killing her) and leaned her head on Andrew's shoulder.

He put his arm around his wife. "Yes, it has. But everything that's led up to this day – the tears, the stress – was worth it. I love you."

Sydney sniffled. "Love you too." She yawned and struggled to keep her eyes open. She and Andrew couldn't wait to leave for their Hawaiian honeymoon. For the first time in a long time, she was going to relax.

When the newlyweds were about to leave for the airport the next day, Simon pulled his daughter aside and hugged her. "Have fun. I'm going to miss you!"

"Thanks, Dad. And listen to Zach – let him reign you in when you get too crazy."

"Are you talking about me?" Off her unimpressed glare, he conceded her point. "Fine, I'll behave."

"Why don't I believe you? But thanks for everything you've done for us over the past year." Sydney kissed his cheek and then walked away with Andrew.

Simon had seen her transition from a little girl to a full grown adult, and while he was a little sad about it, he was also thrilled about how happy she was now. That was what he cared about. Sydney's happiness was above his own and that's the way it always should be.