While engaging in a game of Tongo with Rom, Dax, and a young Ferengi waiter named Pel, Quark is hailed by his leader, Grand Nagus Zek, who has good news for him — Zek has chosen him to act as his chief negotiator in the Ferengi expansion into the Gamma Quadrant. Soon afterward, Zek meets with Sisko and Kira, hoping they will let him use the station for a business conference with the Dosi, a race from the Gamma Quadrant, and they reluctantly agree. Zek then goes to Quark's quarters and instructs him to purchase ten thousand vats of tulaberry wine from the Dosi, a move he feels will establish a strong Ferengi presence. Quark later brags about his profitable assignment to Rom, but Pel, who overhears them, warns him to be wary of Zek's motives, since Zek will be credited for success but Quark will almost certainly be blamed for any failure. Impressed, Quark asks Pel to serve as his assistant, leaving Rom stung. Pel then returns to his quarters, removing his false earlobes and revealing that he is actually a female.

The Dosi arrive on Deep Space Nine, and Quark nervously begins negotiations with Inglatu, the disagreeable leader, and Zyree, an equally difficult female. Things get off to a bad start when Inglatu says he will only sell Quark five thousand vats of wine, then demands to deal with Zek directly, but Pel steps in and firmly states that Quark is the sole contact in the negotiations. Still, Quark is shaken, and is even more upset when Zek informs him that he now wants one hundred thousand vats of wine, but Pel steps in and tells Zek this is a wonderful idea. She then steals a moment alone with Quark and convinces him that he is capable of negotiating this deal. Dax quietly observes the entire interaction and, the next day, questions Pel about her loyalty to Quark, then hears that Pel is not only in love with Quark, she is also a female, having disguised herself as a male to escape the domestic drudgery that is a Ferengi female's legally-mandated lot in life.

The next day, Quark relays to Zek that negotiations did not go well — the Dosi have left the station. Zek becomes enraged, but Pel tells him that they will travel to the Gamma Quadrant and make the deal with the Dosi in their territory. Soon, she is alone on a ship with Quark, and almost reveals her secret as the sexual tension mounts, leaving Quark vaguely troubled. Meanwhile, back on the station, a jealous Rom ransacks Pel's quarters and learns the truth about her gender.

In the Dosi homeworld, Quark boldly approaches Inglatu with the contract, but he still refuses. Quark decides to camp out on the planet to be close to Inglatu in case he changes his mind, putting Pel, who is sharing a tiny tent with him, in an awkward position. Unable to resist, she impulsively kisses Quark, but Zyree enters before he can react, and reveals that Inglatu doesn't have one hundred thousands vats of wine to sell. However, she tips off Quark to the Karemma, an important power in the Dominion, a mysterious group who holds sizable influence in the Gamma Quadrant. Realizing that this information, not the wine, is what Zek really wants, he and Pel return to the station. Quark refuses to talk with Pel about the kiss and goes straight to meet with Zek, who promises Quark a percentage of every Ferengi opportunity in the Gamma Quadrant in exchange for a meeting with a member of the Dominion. Suddenly, Rom interrupts and pulls Quark away, telling him the truth about Pel. Quark promptly faints.

In the Infirmary, Rom reminds Quark that since she wears clothes and tries to earn profit, Pel has violated Ferengi law and should be punished. Afraid to ruin his reputation with Zek, Quark promises to give Rom the bar in exchange for his silence. Quark then visits Pel in her quarters and tells her to leave the station. She tells Quark that she loves him, but despite his feelings for her, he tells her he would not be happy with a non-traditional Ferengi wife. Determined to make her point, Pel confronts Zek and reveals her true identity. Zek threatens to imprison both her and Quark, who is guilty of the Ferengi crime of taking business advice from a female, until Quark reminds Zek that he, too, is guilty. Zek agrees to keep quiet, costing Quark his potential Gamma Quadrant profits. Pel leaves the station to continue her adventures, and Quark is left with nothing but the sadness of his first lost love.