Orlando is the youngest son of the late Sir Rowland de Boys. He's also the younger brother of the nasty tyrant Oliver and lover of Rosalind.
If we think about Orlando's trajectory in the play, he sounds a lot like a troubled teenager. He stands up to his bully of a big brother, picks a fight with a bigger guy, runs away to the Forest of Arden, and then tags up all the trees with poems about his girlfriend. Still, as is always the case, things are a bit more complicated than that.
The first time we meet Orlando, he's fired up and says he's ready to "mutiny" (1.1.23) against his big bro. What's Orlando so angry about, you ask? Well, his father has died and he's been left penniless because of the system of primogeniture, which says that oldest sons get to inherit all of their fathers' wealth while younger sons, like Orlando, get zilch. Wait—it gets worse. Not only did Orlando get shafted in his dad's will, he is also treated like dirt by his older brother, Oliver, who is supposed to be taking care of him:
My father charged you in his will to give me good
education. You have trained me like a peasant,
obscuring and hiding from me all gentlemanlike
qualities. The spirit of my father grows strong in
me, and I will no longer endure it. (1.1.66-70)
Orlando knows he's angry, but here, he doesn't know quite know what to do about it so he vents his frustration by running out and challenging Charles, the court wrestler, to a match. Orlando is the underdog every audience roots for, and miraculously he wins the match, even though Charles has a reputation as a bone-crusher.
Still, Orlando isn't exactly a testosterone-driven meathead. Once he meets the luscious Rosalind, he falls head-over-heels in love. Like Romeo, Orlando responds to this new flood of passion by being a romantic drama-queen. You did notice how he littered the Forest of Arden with sappy love poetry about Rosalind, didn't you? If Orlando were a modern day teenager, he'd probably be running around writing his cheesy verses on the bathroom walls at school. Since he's a fictional character who lives in the Forest of Arden, he tags up all the trees instead. Here's an example, in case you missed one of the gazillion poems hung from the trees in Arden:
From the east to western Ind
No jewel is like Rosalind.
Her worth, being mounted on the wind,
Through all the world bears Rosalind.
All the pictures fairest lined
Are but black to Rosalind.
Let no fair be kept in mind
But the fair of Rosalind. (3.2.88-95)
OK. Orlando's not going to win a Pulitzer Prize for his poetry any time soon. As Rosalind and Touchstone point out, Orlando seems sincere, but this mushy, sing-songy stuff is also really bad poetry. Jaques even begs him to "mar no more trees with writing love-songs in their barks" (3.2.264-265).
Not only that, but Orlando's idea of love is highly artificial. In fact, his poetry and behavior make him look and sound a lot like what we call a "Petrarchan lover." (In other words, he's someone who acts like a guy in one of Petrarch's 14th-century Italian love poems. This involves a lot of dramatic sighing, sadness, and frustration over an unattainable girl who could kill a man with a dirty look. Sound familiar? It should because this is exactly how Romeo behaves at the very beginning of Romeo and Juliet.)
So, it's a good thing that Rosalind is willing to remind Orlando that real love is nothing like the stuff we find in cheesy poetry, fortune cookies, or even some popular poetry. Whenever Orlando gets overly dramatic and silly, she gently reminds him that love is not a Hallmark e-card.
How does she do this? Let's look at an example. When Orlando suggests that his love for Rosalind might be the end of him because her "frown might kill" him (4.1.115), Rosalind says this is not likely to happen. As Ros points out, "Men have died from time to time, and worms have eaten them, but not for love" (4.1.112-113). When Orlando figures out that love is not a Hallmark e-card, he learns how to be the perfect boyfriend/future husband.
Before we dismiss Orlando as some wimpy romantic who lets his girlfriend push him around, though, we want to remember that Shakespeare endows him with plenty of spirit. Not only does he beat up Charles in the wrestling match, he also fights a ferocious lion and saves his brother's life. All around, he's a likable and easy-going guy who might actually be able to handle his brassy, cross-dressing girlfriend.