Winning
Kakashi didn't get the point of a challenge.
When Gai boasted that he could run a race around Konoha walking on his hands, Kakashi said, "No. You can't." And he went back to reading his comics.
"Then are you saying that you can't do it?" Gai demanded.
Kakashi reflected on that. "I can. But I won't."
"If you can, then why not?" Gai asked.
To Gai, the world was full of possibilities.
Kakashi looked up from his comic. "Because it's pointless."
"Reading your comics instead of enjoying this day and being youthful is pointless, too," Gai retorted. "If that's all you've got to say against it, then I challenge you to a race around Konoha on our hands. If you can make it to the top of the Hokage Monument before me using only your hands to walk on, then I'll concede that you could do it and simply didn't want to."
Kakashi sighed. "I can, and simply don't want to."
Gai smirked. "And I think you can't. The challenge starts now, Rival!"
Before Kakashi could come up with a witty retort like 'I'm sorry, what did you say?' Gai did a flip, landed on his hands, and started walking on them as fast as he could.
Kakashi frowned in annoyance, tucked his comic into his flak jacket, and pursued. Walking on his hands made all the blood rush to his head, but it wasn't that difficult. Really. And he was going to win.
To Kakashi, challenges were about winning. What else could there be?
And yet, when he reached the top of the Hokage Monument first, Gai spent a paltry three seconds acting disappointed and then asked Kakashi to get ice cream with him.