I was talking to Rei-mun, and she asked me to explain.
I apologize in advance for any mistakes.
This is my interpretation on his "sad" side.
I invite flamers into my ask box.
1) His childhood.
Tamaki is an illegitamate child, and he knew that very early on. His father was not around very often, and his mother was very ill. Frequently on bedrest. He was innocent because his mother was too. She made sure he kept his innocence too.
Despite his parent's efforts to keep him happy, as well as the staff's, he was still alone. He had no friends his age. From what I read, he had to be home-schooled. His best friend? A stuffed bear named Kuma-chan. His time was filled with toys, games, and his mother.
2) His mother.
His mother was his world. Nothing mattered to him more. And at his very young age, she got severely sick. During that time, he worried. There was no one to console him, but his mother, the woman he worried about. His father rarely visited. And when he did, It was short.
Then, at age 14, the person he cared about most. The only person truly in his world, was taken away from him. Practically forever. Thus was replaced, by a new enviorment that he'd only heard stories about. And those stories were of traditional Japan. So, basically, he knew very little about the country. (I don't know French strereotypes of the Japanese)
3) His personailty.
Ok, this is quite complicated, but I'll do my best.
Tamaki and I have a similar personaility. We both only want the best for others without thinking of ourselves.
With our strong, happy personailty, there is always a painful hardship you've had to endure. In Tamaki's case, abandonment.
He was taken away from his mother at age 14. Then, when brought to Japan. His grandmother openly despised him and called him deragatory names. His father was never around. Always busy with work. They didn't even live in the same house. It was Shima and the other members of the Mansion #2 household who raised Tamaki on.
Ok, now the AU stuff.
4) Unrequited love/The love triangle.
Tamaki already found out early on that Rei loved Kyoya. Yet, he led himself on thinking maybe he could win her over. Maybe she could love him. Kyoya was always away because whenever he wasn't around Rei was with him. He wanted to win her over. So badly.
Then the marriage.
Despite his desires, he couldn't do that to the woman he loved. He couldn't permanently get between two people who loved each other - especially one of them being his best friend.
It all but reminded him of his parents' marriage. He never wanted that to happen. He doesn't want a child to go through the pain he's been through. So he vowed to get them together. He promised to do whatever it took to have true love prevail.
5) Preparations for the marriage.
Tamaki scrambled during this time to figure out a way to get Kyoya and Rei together. As a result, that became his #1 focus. It got in the way of his hosting. Rumors started. Word got out about their engagement. He freaked out. No one came to be entertained by him, he rarely ever got a visitor. His only visitor during that time seemed to be Emilia.
Tamaki was afraid for Rei. He had heard from the other girls that she was the reason Tamaki wasn't himself, and for a time, he had considered shutting Rei out to stop the gossip. It gradually blew over by itself. He continued to worry himself over it.
Kyoya became more hostile with Tamaki. And it broke him. Kyoya meant more to him than life itself. More to him than Rei. He didn't want to lose him over this engagement/marriage.
6) The accident.
All the stress and over-thinking had finally reached it's climax.
Tamaki's over-thinking had led him to believe that this was his fault. He traced it all the way back to the Disneyland trip. If he hadn't forced Rei to go on that trip, then he would've never stepped between them. He put up a strong front because, as his mother told him, if he smiled, they'd smile.
But constantly, he put himself down. He moved into a state of mind where he blamed everything on himself. Though he never showed it because he believed thats what his mother would've wanted. That if he hadn't done anything, none of this would've happened. That the people he cared most about would've been happy.
Secretly, he wishes he died in that accident.
But he didn't. Therefore, he has to continue living to the fullest, as his mother wants.
And that is the sad side of Tamaki's personaility.