Sir Rowland de Boys has recently died, leaving behind sons Oliver and Orlando. Since Oliver's the eldest son, he's inherited just about everything. This includes the responsibility of making sure his little bro finishes school and continues to live the kind of lifestyle he's become accustomed to as the son of a nobleman. (By the way, this lifestyle looks like a sixteenth-century version of MTV's Teen Cribs.)
Oliver, however, treats his little bro like a servant – he refuses to pay for Orlando's education and never gives the kid any spending money. Also, he tells the local court wrestler it would be a good idea to snap Orlando's neck, but Orlando doesn't know about this. Naturally, Orlando is ticked off that Oliver treats him so badly and he's ready to "mutiny" against his older bro. Instead, he channels all of his pent up anger into a wrestling match, where he beats the court wrestler to a bloody pulp.
Orlando's wrestling skillz catch the eye of a local girl named Rosalind, who has her own family drama to worry about. (Ros is the daughter of Duke Senior, who used to rule over the French court but was overthrown by his snaky, backstabbing brother, Duke Frederick. Because Rosalind's dad is living in exile in the Forest of Arden, Rosalind has been crashing at the palace with her BFF/cousin, Celia. Did we mention that Celia is the daughter of snaky, backstabbing Duke Frederick? And you thought your family had issues…)
Rosalind thinks Orlando is the dreamiest boy she's ever laid eyes on and Orlando feels the same way about her. The two fall in love faster than you can make Ramen noodles. Rosalind gives Orlando her necklace, which means the two are officially an item.
Things go downhill from there. Orlando finds out that his big brother Oliver is planning to burn his house down (with Orlando in it), so he runs away to the Forest of Arden. Since he's broke he takes his old family servant Adam along for the adventure. This is a good thing because Adam ponies up his entire life savings to help cover the costs of the road trip.
Meanwhile, Duke Frederick decides that he doesn't like the fact that Rosalind is more popular than his daughter, Celia. So, Duke Frederick 86'es his niece from his court.
Rosalind decides to run away to the Forest of Arden, which, apparently, is the destination of choice for exiles. To avoid being the target of rapists and thieves, Rosalind decides that she'll dress as a boy and call herself "Ganymede." Cousin Celia is so devoted that she decides to run away too and she disguises herself as "Ganymede's" sister, "Aliena." (As in Celia is now alienated from her father.) Just for kicks, the girls decide to invite the court fool, Touchstone, along with them.
Cut to the Forest of Arden, where we meet Rosalind's dad, Duke Senior. He's a pretty happy-go-lucky guy for being a banished duke, and he tells us that Arden is a lot like the garden of Eden (except for the fact that Arden is lot colder and windier).
Meanwhile, Orlando and his servant Adam are starving because they forgot to watch Man vs. Wild and have no idea how to find food in the forest. Adam passes out and Orlando promises to find him some dinner. Luckily, Orlando stumbles upon Duke Senior and his band of "merry men" sitting down to a mouth-watering banquet. Orlando crashes the party and threatens to kill everyone if they don't give him something to eat, like, right now. The Duke is all "chill out, and bring Adam, too." Orlando and Adam make a ton of new friends at the banquet, including "melancholy" Jaques.
On the cross-dressing front, things are good for Rosalind/Ganymede as she settles into the Forest of Arden. She meets a shepherd, Corin, who gives Rosalind a hot real estate tip about a cottage that comes with its own flock of sheep and plenty of land for grazing. Rosalind/Ganymede and Celia/Aliena don't waste any time going country – they buy the cottage and make friends with the locals. Among their new rustic pals are a lovesick shepherd named Silvius and the woman he loves, Phoebe. (By the way, Phoebe hates Silvius.)
Yet, love is definitely in the air. Rosalind discovers poems (stuck to trees) that a mysterious lover has penned – about her! The poems are pretty awful and they're full of silly clichés about love, but Rosalind doesn't care when she finds out the poems have been written by none other than dreamy Orlando.
Before we know it, Rosalind bumps into Orlando in the forest. Instead of coming clean about her true identity, she stays in her "Ganymede" disguise and becomes pals with Orlando. (That way, she can pump Orlando for information about how he really feels about her.) Orlando confesses to "Ganymede" that he's head over heels for Rosalind. "Ganymede" then generously offers to pretend to be Rosalind, so that Orlando can practice all of his best moves in the romance department. Orlando, who has no idea "Ganymede" is actually the girl he loves, takes the bait and even participates in a pretend wedding. Aww.
As it turns out, though, Orlando is under the impression that romance should look something like a sappy, 14th-century Italian Hallmark card, so Rosalind/Ganymede has got her work cut out for her. She rolls up her sleeves and teaches Orlando how to be a good boyfriend/future husband without ever revealing her true identity.
Meanwhile, the local shepherdess, Phoebe, has fallen in love with "Ganymede" and wants to marry "him." Also, Touchstone has managed to find a not-so-bright country girl, Audrey, who is willing to get hitched.
The action comes to a head when Rosalind/Ganymede bumps into Orlando's mean brother, Oliver, in the forest. We learn that Oliver came to the forest to kill his little bro, but, when Orlando saved his life from a ferocious lion, Oliver repented and decided not to kill his kid brother. This is good news, because Oliver and Celia fall in love, about two minutes after meeting. (What? Things happen fast in Arden.)
Seeing Oliver and Celia so happy makes Orlando sad. Even though it's been fun pretend-romancing "Ganymede," Orlando says he can't live another day without the real Rosalind. "Ganymede" takes pity and promises Orlando that he'll get to marry his girl the very next day. Then "Ganymede" promises that all the lovesick characters will be getting hitched tomorrow.
The next day, everyone gathers around in the forest. "Ganymede" enters and makes Silvius, Phoebe, and Orlando promise to do whatever he says: Orlando must swear to marry Rosalind if Ganymede can produce her; Phoebe must promise to marry Silvius if she decides she doesn't want to marry Ganymede; Silvius must swear that he will marry Phoebe if Phoebe will have him. When Rosalind whips off her "Ganymede" costume and reveals her true identity (surprise!), her plan falls neatly into place.
Before all of the couples get a chance to smash wedding cakes into each others' faces, Orlando's brother, Jaques de Boys (not to be confused with melancholy Jaques) shows up with news that Duke Frederick has decided to give back Duke Senior's dukedom. Apparently, Frederick entered the forest ready to kill his brother, but met a "religious man" along the way and experienced a sudden conversion. (Like we said, things happen fast in Arden.)
Duke Senior can't wait to return to court and promises to restore all the exiles to their proper social stations – including his new son-in-law, Orlando, who will inherit his dukedom. For now, though, he says that everyone should party like it's 1599.
And they all live happily ever after. (Except for melancholy Jaques, who decides to hang out by himself in a cave.)