Later on there will be other missions such as “Wildlife Preservation” where you can high five him, too! You can only bring him into the high five position once! Leave the game (without saving) if you mess up. Quickly hit his hand with a melee attack. After completing the quest press Trianlge (PS3) / Y (X360) to prompt him into the high five position. He will give you a really short quest where you have to open a cupboard right infront of him. The mission can be started by talking to Claptrap in Sanctuary. This can be done after completing a side mission called “Claptrap’s Hidden Stash”.