Gene met up-and-coming costume designer Oleg Cassini in the last months of 1940. She was still a comparative newbie in Hollywood. At the beginning of the year, she had been appearing in The Male Animal on Broadway; by the time she met Cassini, she had filmed three films at 20th Century-Fox, although she had not yet done a starring role. Cassini was under contract to Paramount Pictures as a costume designer who had previously studied under Jean Patou in Rome. The two met at a dinner party hosted by Johnny Maschio and Constance Moore; soon after, Cassini asked Gene for a date on New Year’s Eve. She broke a previous date with a purported illness, and agreed to ring in 1941 with him. They soon began dating consistently and frequently.
Cassini began to give Gene clothing advice; she had previously designed most of her own clothes. He would design her wardrobe in a good portion of her films from then on out, even after their marriage crumbled. She had dated many men before and since arriving in Hollywood, and was not certain this was a relationship she wanted to take toward marriage. Gene said later that any doubts she still held dissipated during production of Belle Starr, her first starring role. She suffered an eye infection during filming that caused her eyes to become swollen, watery, and red, puffing up the point that she could barely see. Cassini assured her he did not care, telling her that “it doesn’t matter, Gene. You always look beautiful to me.”
The two met opposition from both Gene’s family and their home studios when marriage entered the picture. The Tierneys opposed the marriage, Fox did not want of their most eligible starlets married off so soon, and Paramount claimed he wasn’t taking his work seriously. Eventually, Paramount Pictures fired him. Howard Tierney threatened to declare his daughter mentally unstable if she married Cassini, and consequently sent brother Howard Jr. out to Hollywood to talk her out of it. Gene and Cassini decided to marry regardless, being thwarted in one trip to Las Vegas by inclement weather. Belle Tierney was still living in Hollywood with Gene, and continued to oppose the match, beginning to attack Cassini’s character. Gene backed away from the elopement for a time and tried to date a few others. It didn’t work. They resumed their elopement plans, and flew to Las Vegas on a commercial flight. Then they made their way to the home of Judge Brown, and were married on June 1, 1941, with Gene’s earring used as a wedding ring.
Back from the elopement, a hounded Gene gave calm statements to the press, stating that her family would eventually get over their aversion to the marriage. They did not. In private, her mother had flown back to New York, and both her parents stated goals of having the marriage annulled. Gene’s relationship with her mother would remain strained for years, and though her relationship with her father was already broken over a financial matter, the marriage feud would irrevocably seal the fate of their correspondence. They barely saw each other. Cassini’s parents, however, both gave the couple their blessings and visited Hollywood to deliver them in person.
Hollywood society did not accept the newlywed Cassinis as a couple; if Gene received social invitations, they were addressed to Miss Gene Tierney. Fox sent Gene out on loan to United Artists for Sundown, and she left for New Mexico location filming two weeks after their wedding. The couple tried to stay in touch via phone during the shoot, but one hopeful factor would introduce itself soon after. Oleg was hired to design the cast’s wardrobe for The Shanghai Gesture, one small token of acceptance to come. They were also invited to the home of Tyrone Power as a couple, for a large dinner party.
The couple had their first child in 1943, when Antoinette Daria Cassini was born on October 15. She was premature, already had blurred vision, and was partially deaf. Due to accidental contraction of rubella during her pregnancy, Daria’s mental development would be delayed. She was placed in the Langhorn School at four years old, and spent most of her life in a variety of institutions. Daria’s issues and the stress of decisions to be made concerning her welfare put stress on the Cassinis’ fledgling marriage.
Oleg and Gene had separated by early 1946, and she decided to file for divorce soon after. During their separation, Gene became involved with John F. Kennedy, then running for Congress, and Tyrone Power. For a short period, she even tried a relationship with Howard Hughes again. The Cassinis reconciled in early 1948, and Gene called off the divorce. She had received an interlocutory degree but did not file for the final degree, nor did Cassini. Oleg had felt treated as ‘Mr. Gene Tierney,’ which contributed to the separation, and he had also wandered romantically more than once. Now, Oleg had success as a designed on his own, with a business established in New York, and their marriage resumed on calmer terms. They had a second child, Christina, born on her mother’s birthday in 1948.
Their second go at marriage lasted for a shorter period than the first. Gene was frequently filming another movie, and Oleg had his business to run in New York. In a last ditch attempt, they moved to Connecticut, where Oleg could commute to work and they could try the suburban dream. But that soon dissolved as well; as Gene wrote later: “Oleg had a business to build. I had a career to pursue.” Each were being pulled in opposite directions by their work, and neither party was thrilled by seeing their spouse in the company of handsome actors or slinky models.
Gene filed for divorce in early 1952, and requested custody of Christina and Daria. Their divorce settlement stipulated that half of Oleg’s assets at the time of his death would be bequeathed to their two daughters, a term that would be contested in court over fifty years later. It also stated that the only persons allowed in Oleg’s residence when their daughters visited would be his then spouse and any other children. Their divorce was finalized in 1953.