Orlando is the youngest son of the deceased Sir Rowland de Boys.
His eldest brother Oliver mistreats him, refusing to educate him as he does the second son Jaques. He is an excellent wrestler, noble, well-loved by all who know him, proud of his birth and intelligent, as well as young and tongue-tied in front of women. He falls head over heels in love with Rosalind on speaking to her. Gaining Duke Frederick’s enmity for beating his favorite wrestler and being Sir Rowland’s son, and with his eldest brother planning to burn him to death in his sleep, he flees to the Forest of Arden with Adam. He is faithful to the faithful old man, carrying him on his back when he can no longer walk. Starving, Orlando attempts to rob Duke Senior and his men of food, only to discover that they will share it willingly. He is a very bad poet, and writes poems in praise of Rosalind that he hangs up on the trees around the woods. He does not listen to criticisms of his writing, but on meeting Ganymede accepts to play the game of learning how to woo a woman, learning in the process to love genuinely rather than playing at it. Coming across his brother in danger from both a snake and a lioness, he almost leaves Oliver to be killed, but his nobility of spirit prevents him from doing so. The two are thereby reconciled. Orlando is taken about at the fact that Oliver falls in love and convinces Aliena to marry him as quickly as he does. He becomes rather confused about Ganymede, but trusts him for the sake of his love for Rosalind. He has chestnut hair and no more than the beginning of a beard.