This one is super simple to do in the first "Dungeon", Jack of Dust, and the early achievement will teach you about your best friend in the combat portions of this game,
, which is your roll. Using a pseudo-Arkham system, pummel on your foes and roll away from danger in quick succession in three separate combat encounters. The encounters DO NOT have to be consecutive and you MUST be on the """medium""" difficulty or higher, won't pop on Easy.
This can be made easier using your other best friend,
, your block. However, you cannot block without a shield, and the indicators for enemy attacks will also not appear. The game is merciful in granting you the "Mister Lionel" encounter (it was my second encounter card), which if you reply with "Ask Him What He Needs", will grant you a shield.