Why John Cusack Never Married — Despite His Secret Rumored Flings

John Cusack spent decades as a Hollywood mainstay, starting out as a teen idol in the '80s and deepening his breadth with unconventional, quirky parts into the '90s and '00s. Cusack has largely stepped away from Hollywood since, but the former A-lister managed to keep his love life under wraps even at the height of his fame. While speculation about flings and confessions from old flames have surfaced over the years, the "Being John Malkovich" actor remained among the celebs who never got married. In his case, he just never felt like bowing down to societal convention.

When Elle asked whether he could answer why he never got married in five words, he responded that he could do it in seven. "Society doesn't tell me what to do," he said in the 2009 interview. Cusack has never been afraid to voice controversial opinions, and his answer suggests he views marriage as an unnecessary — and possibly outdated — path for a relationship. While he has been romantically linked to high-profile women, including Jennifer Love Hewitt, Uma Thurman, Minnie Driver, Ione Skye, and Jodi Lyn O'Keefe, Cusack has always kept his romances out of the spotlight.

There has been plenty of speculation, though. Reports went so far as to claim that Cusack came close to becoming engaged to O'Keefe, though he never went through with it. "He's never felt the need to get married. She hoped for years he'd change his mind, but she's done wasting her energy," a source told Star Magazine in 2009 (via ONTD). He didn't just talk the talk, but his views on the matter may have been influenced by negative experiences early in his life. 

John Cusack became disillusioned with relationships early on. In high school, he wasn't among the popular guys. But that changed completely as soon as he started acting. Cusack made his film debut in the 1983 comedy "Class," when he was 17 and still in school. As if a switch had flipped, he became interesting. "I didn't really get much play with the ladies. But then, all of a sudden, when I did a few films, I was taking the jocks' girls," he said on NPR's "Fresh Air" in 2001.

That experience taught him to take a skeptical approach to his love life, and he noted that it made it hard for him to trust the intentions of those who showed interest in him. "I really wasn't highly regarded in high school and then when I started making movies, of course, I was, which was another valuable lesson," he told host Terry Gross. While he enjoyed the newfound attention, Cusack realized soon enough that it exposed him to situations he was ill-equipped to handle. "If you're a movie star, there's a cycle you go through: adoration, adulation, you're used, and then you're discarded," he said in the Elle interview. 

Cusack was stuck in that sequence for quite some time, until he became aware of the pattern. In due time, he became better at reading people and avoiding those kinds of relationships. Unfortunately, despite the many success stories of couples who met on-set and stayed together, he doesn't think that dating within the industry is a decent alternative to his earlier experiences. "Actors go out with actresses as a form of self-flagellation," he told Elle.