I am glad I have found this napkin,
This was her first remembrance from the Moor.
My wayward husband hath a hundred times
Wooed me to steal it, but she so loves the token
(For he conjured her she should ever keep it)
That she reserves it evermore about her
To kiss and talk to. I’ll have the work ta’en out
And give ʼt to Iago. What he will do with it
Heaven knows, not I.
I nothing but to please his fantasy.(3.3.297–306)

Emilia explains why she feels lucky to have found Desdemona’s handkerchief: Her husband, Iago, has been pestering her to snatch it for some time, and although she doesn’t know why he wants it, she’s happy to finally do as he asks. The handkerchief, a gift to Desdemona from Othello, symbolizes so much more than a mere token of affection. To Othello, the handkerchief symbolizes fidelity and his giving it to Desdemona represents a promise that he will be true to her, and a request that she stay true to him. Iago, understanding the object’s significance, plans to turn the token of love into a tool of destruction.

If it be not for some purpose of import,
Give ‘t me again. Poor lady, she’ll run mad
When she shall lack it.(3.3.324–326)

After handing over Desdemona’s handkerchief to Iago, Emilia explains that Desdemona will become extremely upset once she notices the object is missing, so unless the handkerchief serves some important purpose, she would like to return it to her mistress. Emilia recognizes the powerful love and loyalty Desdemona feels for Othello, and she knows that the handkerchief symbolizes these emotions. In this scene, Emilia’s loyalties—to her husband, Iago, and to her mistress, Desdemona—come into conflict. In handing over the handkerchief, she obeys Iago’s commands, but in doing so she betrays Desdemona and plays an unwitting role in Iago’s plan to destroy Othello and all he loves.

I will in Cassio’s lodging lose this napkin
And let him find it. Trifles light as air
Are to the jealous confirmations strong
As proofs of holy writ. This may do something.
The Moor already changes with my poison.(3.3.329–333)

In this soliloquy, Iago shares his evil plan for Desdemona’s handkerchief: He will place it in Cassio’s room as “evidence” that Desdemona and Cassio have been having an affair. Iago understands that a gift such as a handkerchief might be a mere trinket to some, but bear profound meaning to others. As a jealous man, Othello invests the handkerchief with great meaning. Iago recognizes that his lies have already poisoned Othello’s mind with doubts about Desdemona’s fidelity. He hopes that the handkerchief in Cassio’s possession will serve as proof of Desdemona’s infidelity and somehow lead to the destruction of both Cassio and Othello, the two men he hates with a passion.

Believe me, I had rather have lost my purse
Full of crusadoes. And but my noble Moor
Is true of mind and made of no such baseness
As jealous creatures are, it were enough
To put him to ill thinking.(3.4.21–25)

Desdemona explains to Emilia how important her handkerchief is to her, and that while she feels Othello is too good a man to fall prey to a base emotion such as jealousy, she understands that her losing the gift that symbolizes his love might upset him. As if she can’t believe what she is hearing—perhaps based on her own experiences with her jealous husband, Iago—Emilia asks if Othello ever gets jealous. Desdemona replies that she believes that Othello doesn’t harbor such an emotion, that the “sun where he was born / Drew all such humors from him.” Ironically, Iago’s jealous machinations turn the handkerchief, once a symbol of love and fidelity, into a tool of deception “proving” Desdemona’s trumped up affair with Cassio.

She told her, while she kept it
ʼTwould make her amiable and subdue my father
Entirely to her love, but if she lost it
Or made gift of it, my father’s eye
Should hold her loathèd and his spirits should hunt
After new fancies.(3.4.55–60)

Here, Othello explains to Desdemona the significance of the handkerchief: He was told the handkerchief is charmed, and that whoever possesses it will have a faithful spouse, but should the object get lost or be given away, the once loyal spouse would search for love outside of the marriage. Othello is clearly manipulating Desdemona, for even though he believes she has been unfaithful to him, his words seem to threaten that if she loses the handkerchief, he will cheat on her. Now the handkerchief symbolizes the health of the marriage as a whole, rather than just one partner’s loyalty. Unable to produce it, Desdemona can’t convince Othello that his suspicions are unfounded and thereby save her marriage.