I own none of the Smallville characters if I did I would have pushed Lana off a cliff in the first season.
Oliver walked through the doors of Queen Manor tiredly, sighing as he realised that his day was about to become even more difficult. Of course how could it not be more difficult he thought when your best friend the girl that you're secretly in love with is immune to your charms?
Sighing again Oliver thought about how it must have been one of the stupidest ideas he'd ever had inviting Chloe to live with him. "For the benefit of the league." He'd said, little did he know of the acute torture that it would be living in her presence everyday and not being able to do anything about it.
Suddenly he realised that Chloe wasn't there, and she was always there when he came home, whether it was from a long day at Queen Industries or from patrolling as the Green Arrow by night, she was always there.
Searching the entire manor the he finally found her next to the pool, nearly catatonic. Kneeling next to her he called,
"Chloe. CHLOE. CHLOE! What's wrong, what happened?"
Chloe just continued to stare blankly at the pool.
"Please Chloe tell me what's wrong?"
After a few more agonising minutes she finally spoke,
"I had a sister Ollie now she's dead."