Gloria Trillo has the distinction of being the woman in the briefest and most intense affair of Tony's life. No ordinary goomara, she was a smart, beautiful career woman, a top sales rep at Globe Mercedes. She was also highly independent, capable of traveling to Morocco alone and on her own dime. Gloria was passionate and impulsive - bordering on the compulsive; she once arranged for Tony to meet her at the zoo, where she seduced him in the reptile house. Gloria was like nothing Tony had ever seen before, and he told Dr. Melfi that said she made him "feel better than your Prozac and therapy bullshit combined."
But Gloria had her dark side as well. That Tony met her in Dr. Melfi's waiting room should have been an indication of it. Gloria was being treated for severe depression, exacerbated by a string of failed relationships, and her relationship with Tony was eventually added to that string. Gloria became jealous and demanding, and the last time she saw Tony she threatened to call Carmela. Enraged, Tony almost strangled her on her kitchen floor, with Gloria spitting in his face and begging him to go through with it.
Ultimately, Gloria - nothing if not self-sufficient - took matters into her own hands. Some months after her breakup with Tony, she committed suicide. She hanged herself from a chandelier, without leaving a note.