Just try it...

YOU WON!
Just two words on paper, nothing else. Dean didn't like Laila, and Sam felt fed up with him and said something he regrets. "If you can't at least try to know my daughter before you judge her then leave." So, yeah he won the fight but for what price.
He wasn't surprised to find Laila in the library. "He left, didn't he?" Sam just nod. They spend the whole afternoon teaching her how to play chess. Because his daughter is very smart, he found out that she beat him very soon, and he didn't mind it at all.