Willie Nelson’s Dating History: From Shirley Collie to Annie D’Angelo

The fourth time, it turns out, really was the charm for Willie Nelson.

The legendary singer-songwriter has never shied away from admitting that he made plenty of mistakes in his personal life. But when it comes to marrying his wife of more than three decades, Annie D’Angelo, Nelson is unequivocal. It was, he says, “about the smartest thing I ever did.”

Before finding lasting love with D’Angelo, Nelson had been married three times. He first wed his teenage sweetheart, Martha Matthews, in 1952. That marriage ended in 1962. He then married fellow musician Shirley Collie in 1963; they divorced in 1971. That same year, Nelson married Connie Kopeke, a relationship that lasted until 1988. Across those four marriages, the “On the Road Again” singer is the father of eight children, two of whom he shares with D’Angelo, whom he married in 1991.

Despite his earlier marriages ending, Nelson has long emphasized the respect and love he continues to hold for his former partners, especially in their shared roles as parents. In his joint memoir Me and Sister Bobbie: True Tales of the Family Band, he famously wrote that the phrase “former wife” simply doesn’t exist in his vocabulary.

“I’ll always love all my wives,” Nelson wrote. “There’s no such thing as a ‘former’ wife. Once in your life, a wife never leaves.”

Still, he doesn’t shy away from acknowledging regret. Reflecting on his past, Nelson expressed remorse for the pain he caused Martha Matthews, Shirley Collie, and Connie Kopeke. “I regret the pain I caused Connie — and Martha and Shirley before her — and have no excuses,” he wrote. “But love is love, and in the mid-’80s I fell head over heels in love with Ann Marie D’Angelo, called Annie. I’d never met a woman like her before.”

Nelson married Martha Matthews at just 19 after being discharged from the Air Force in 1952. The couple welcomed three children — daughters Lana and Susie, and son Willie “Billy” Hugh Jr. — before divorcing a decade later. Matthews died in 1989 at age 53.

In the early 1960s, Nelson grew close to singer and yodeler Shirley Collie, whose hit “Willingly” featured his vocals. They married in 1963, but the relationship unraveled years later after Collie discovered Nelson’s infidelity — including the birth of a child with another woman. The pair divorced in 1971. Collie died in 2010 at age 78.

Nelson’s third marriage, to Connie Kopeke, began while he was still married to Collie. He and Kopeke welcomed their first daughter, Paula, in 1969 and married in 1971. A second daughter, Amy, followed in 1973. Though their life was relatively quiet at first, Nelson’s rising fame eventually strained the relationship. His affair with Annie D’Angelo, whom he met while working on the film Stagecoach, ultimately led to the couple’s divorce in 1988.

With D’Angelo, however, Nelson found something different. Though their connection was immediate, she insisted on taking things slowly, wanting to be certain he was truly free. “She didn’t care about me being a celebrity,” Nelson wrote. “She was whip-smart, artistic, politically sharp, and had an energy that could light up a room.”

The couple welcomed sons Lukas in 1988 and Micah in 1990 before marrying in 1991. Both have gone on to pursue music careers — Lukas as the frontman of Promise of the Real, and Micah under the stage name Particle Kid.

Today, when Nelson isn’t on the road, he and D’Angelo run their cannabis brand, Willie’s Reserve. In a May 2023 interview with PEOPLE, Nelson summed up the woman who changed his life: “I call her my pet rattler,” he said affectionately. “She’s my lover, my wife, my nurse, my doctor, my bodyguard.”