Alessandra is introduced in The Jewel of Denial, when Dan's old mentor Noah Shapiro introduces them at his office. Dan is looking for advice on how to handle the upcoming release of Inside, and Noah advises him to just let it come out without making a fuss. When Dan later returns to the office, Alessandra lets it slip that Noah is planning to take credit for writing Inside. In an attempt to stop him, Dan crashes his dinner and learns it was all a ruse to get him to take credit for his own work. In Memoirs of an Invisible Dan, Alessandra sets up Dan's book release party, where she meets Rufus, Lily, Chuck, Serena, Blair, and Louis. Once everyone abandons Dan, she introduces him to the press. She later gets Dan an interview with New York 1 and is able to get Harvey Weinstein interested in the movie rights, but they lose after Serena sabotages their plans (The Fasting and the Furious).
In Rhodes to Perdition, Dan spends hours arguing with an online Twitter hater and eventually decides to track them down. He finds the address attached to the account is Alessandra's, and that she started the account to drum up book sales. After they talk, they sit side by side and take turns being the hater and the lover of Inside. At Chuck's Valentine's Day party, a drunken Alessandra attempts to flirt with him but he rejects her. However, he changes his mind and hooks up with her after seeing a picture of Blair kissing Dan (Crazy Cupid Love). After their initial hookup, they continue to do so as Chuck is looking for a way to destroy Dan. He sends her a chanteuse scarf and upon visiting her office, seduces her into sends Dan's proposal on to the editor without reading it. After they hook up, she learns that the proposal the editor received was a plagiarized book and she hurries to tell Dan. She instructs him to go home and rewrite his proposal as fast as he can to avoid being dropped, and he notices her scarf. She doesn't say who it's from, but Dan quickly figures out it was from Chuck (Cross Rhodes). In Raiders of the Lost Art, Alessandra tells Dan that her friend Lucia has a surprise for him and asks him to cancel his lunch plans with Blair to meet with her. When he does, he learns that Lucia is inviting him to The Writer's Institute in Rome, Italy for the summer. However, Dan is insecure over his relationship with Blair and declines. In The Fugitives, Alessandra calls Dan to try and convince him to take the fellowship in Rome, Italy over the summer.
- Alessandra is also the publicist of Dan's old mentor, Noah Shapiro.
- She is single.
- Her twitter, @IHateHumphrey, actually exists in real life.