Why Renée Zellweger Is Haunted and Humiliated by First Marriage to Country Singer Kenny Chesney 

OK! can reveal Renée Zellweger is still confronting the long shadow of her four-month marriage to country singer Kenny Chesney as friends say the brief union continues to shape her personal decisions nearly two decades later, despite her settled life with British TV presenter Ant Anstead.

Zellweger, 56, the Oscar-winning actress best known for Bridget Jones's Diary, married Chesney, 57, in May 2005 after a whirlwind romance that lasted just five months.

The marriage was annulled four months later, with Zellweger citing "fraud" in court papers, a term she later said was legal language rather than a literal accusation.

The episode became a defining showbiz moment of the era and, according to those close to the actress, has remained a private source of embarrassment that still influences her approach to commitment.

Zellweger has been in a relationship with Anstead, 46, since 2021, after the pair met while filming Celebrity IOU Joyride.

The couple has since built a shared life and bought a home together in 2023, and Anstead has publicly praised Zellweger, recently calling her "iconic" after a statue of the star was unveiled in London.

Yet friends say the prospect of marriage has reopened unresolved feelings linked to her first experience of it.

One source close to Zellweger told us: "Time has not completely softened the impact of that marriage for her. The speed with which it ended, and the very public way it was dissected, left a lasting mark. It still resurfaces whenever her private life is mentioned, and that lingering association continues to affect how she approaches the future."

Another source said: "The annulment effectively became a defining shorthand for that period of Renée's life. It lingered far longer than the marriage itself and continues to shape how she is perceived, something she has never entirely been able to move beyond."

Chesney's recent memoir, Heart Life Music, has also brought renewed attention to the marriage. In the book, the singer reflected on past relationships and his inability at the time to prioritize them over his career.

Friends of Zellweger's say the timing has been painful, reviving a chapter she would rather leave closed.

One source said: "She was deeply uncomfortable seeing that period of her life brought back into the spotlight. Revisiting the marriage stirred emotions she thought she had put to rest and left her feeling reduced once again by a chapter she believed was firmly in the past."

Despite those feelings, Zellweger's relationship with Anstead has deepened. She has become closely involved with his children from previous relationships, including Amelie, Archie and Hudson, who regularly stay at the couple's home.

Friends say Zellweger sees a future with Anstead and values the stability of their family life, but remains cautious about formalizing it.

A source close to the couple said: "She feels deeply settled and secure in her relationship with Ant, but the prospect of marriage still provokes a sense of unease. When the topic arises, she instinctively pulls back, not because she questions the relationship, but because past experiences have left her wary."

Another insider added: "Marriage has been an open topic between them for a long time. Ant has made it clear he is ready to take that step, but it is Renée who remains cautious and has slowed the pace."

Those close to Zellweger insist the hesitation does not reflect a lack of commitment.

One friend said: "She harbors a quiet fear that formalizing the relationship could disrupt something that currently feels stable and fulfilling. Even though she recognizes that concern is not entirely logical, the emotional impact of her past still weighs heavily on her."

Anstead, who has been married twice before, is said to be patient. A source said: "He is acutely aware of why she feels hesitant and has chosen not to push her. He has been clear that he is willing to give her as much time as she needs, because he values the relationship and believes it is worth waiting for."