What many viewers might not realize about Judge Jeanine Pirro — the fiery Fox News host known for her commanding presence on The Five — is that behind her tough exterior lies a self-described hopeless romantic. Her career has been defined by sharp wit, courtroom confidence, and political conviction, but her personal life tells a quieter, more melancholic story. Pirro’s last known relationship was with her ex-husband, attorney Albert J. Pirro, whom she divorced in 2013 after decades of marriage.

Since then, she’s had her share of dates and brief romances, but none that have truly lasted. In a candid interview with the Daily Mail in April 2025, she admitted with surprising vulnerability, “I have been divorced for 14, 15 years and I have dated. I’ve had many fabulous men that I’ve dated. Fabulous. But whether I’ve changed or they’ve changed, it hasn’t worked out.” It was a rare glimpse into the loneliness that sometimes lingers behind her polished television persona.

For someone who has built a career out of exuding strength and independence, Jeanine Pirro doesn’t measure her worth by whether or not she has a partner. Her success is undeniable: a former Westchester County judge, district attorney, and one of Fox News’s most recognizable faces. Yet, she admitted that not having someone to share her social life with occasionally stings. “You know when you go alone you wear like a business suit,” she explained.

“You know, you wear a Dior or a McQueen. But I would like to put on a pretty dress and go with someone. I would like to be feminine and not be the tough girl all the time.” The confession revealed a softer side — a woman yearning for companionship, not out of need, but out of the simple human desire to feel seen beyond her reputation and résumé.

Her yearning for connection contrasts sharply with the emotional wreckage of her past marriage, which was as dramatic as any courtroom trial she’s presided over. Jeanine and Albert Pirro seemed, at least from the outside, like a power couple destined for permanence. They met in the 1970s, both ambitious and passionate, and married in 1975. Together they raised two children, balancing law, politics, and high-profile careers. For decades, their partnership appeared unshakable. But behind the facade of success and stability, fractures were forming — ones that would ultimately shatter their marriage and leave emotional scars that Jeanine still carries.

The unraveling began in the late 1990s when Albert Pirro became embroiled in legal trouble and scandal. He was accused of tax fraud and, more devastatingly for Jeanine, of infidelity. The revelation that Albert had fathered a child with another woman was a public humiliation for someone whose professional image depended on integrity and discipline. The affair was more than a betrayal; it was a deeply personal wound inflicted in full view of the media spotlight.

Albert’s own comments only deepened the pain. “Do I think that I would like to have more attention at home? Yeah,” he told New York Magazine, in what many saw as a thinly veiled justification for his affair. “If you’re not going to get attention at home, I think you really need to make some decisions about your future.”

Albert didn’t stop there. He later claimed that Jeanine’s political ambitions had harmed their family’s finances and stability. “Look, the decisions that were made by her have a very significant negative impact on the economic status of our family,” he said — a statement that seemed to shift blame away from his own misconduct. To the public, it painted the picture of a man unwilling to take responsibility; to Jeanine, it was another twist of the knife. Those close to her have said that the experience hardened her, teaching her that independence is the only true safeguard against disappointment. Yet, even after the pain of betrayal, she has never sounded bitter — only wistful.

Over time, Jeanine rebuilt her life. Professionally, she soared. Her legal expertise, charisma, and willingness to speak boldly made her a household name at Fox News. Personally, though, her romantic life never quite recovered. While she occasionally hints at dating or meeting new people, the connections haven’t lasted. Friends describe her as someone who enjoys companionship but struggles to find men comfortable with her success and strong will.

It’s a dilemma faced by many powerful women — admired from afar but often misunderstood up close. Jeanine herself has acknowledged this in interviews, admitting that she sometimes wonders if her independence intimidates potential partners. “I don’t want to be the tough girl all the time,” she confessed. “I just want to be myself.”

Now in her seventies, Jeanine Pirro remains unapologetically herself: confident, outspoken, and unafraid to stand alone when necessary. Yet, her reflections on love reveal a quiet vulnerability that contrasts with her television persona. She may attend glittering galas in tailored Dior suits, but beneath the glamour, she is still the woman who wishes she could slip into a gown, take someone’s arm, and just be “Jeanine,” not Judge Pirro or the Fox News firebrand. The irony, of course, is that the same qualities that make her formidable — her intellect, drive, and independence — are the ones that seem to have cost her the traditional romance she once dreamed of.

In the end, Jeanine Pirro’s love life tells a story that’s as complex as she is: one of ambition, heartbreak, and resilience. She has weathered public scandal, private disappointment, and the solitude that often comes with success. Yet she endures — still laughing, still working, and still holding onto the faint hope that somewhere, someone might see past the headlines and find the woman behind the legend. It’s a bittersweet truth: Jeanine Pirro may have conquered the courtroom and the television screen, but in the quiet moments between broadcasts, her heart remains the one case she’s yet to win.