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

Willie Nelson has been married four times, including his marriage to his current wife, Annie D’Angelo

The fourth time's a charm for Willie Nelson.

The legendary country singer-songwriter has admitted that he's made his fair share of relationship mistakes over the years, but marrying wife Annie D'Angelo was "about the smartest thing [he] ever did."

Prior to D'Angelo, Nelson was married to his teenage sweetheart, Martha Matthews, from 1952 to 1962. He then married singer Shirley Collie in 1963 before their split in 1971. He and Connie Kopeke got married that same year, but the two divorced in 1988. The "On the Road Again" singer has eight children from his four marriages, two of which he shares with D'Angelo, whom he's been married to since 1991.

Though his past marriages didn't work out, Nelson has never wavered in respecting the relationship between his children and their respective mothers. He also still has love for his previous partners, noting in his joint memoir, Me and Sister Bobbie: True Tales of the Family Band, that the words "former wife" aren't part of his vocabulary.

"I'll always love all my wives. I've always said that there's no such thing as a 'former' wife. Once in your life, a wife never leaves," he wrote. However, Wilson felt some magnetic force with D'Angelo, and for any "pain" he's caused toward his ex-wives, he expresses "regret."

"I regret the pain I caused Connie — and Martha and Shirley before her — and have no excuses," he continued. "But love is love, and in the mideighties I fell head over heels in love with Ann Marie D'Angelo, called Annie. Never had met a woman like her before."

Here's a look back at Willie Nelson's dating history.

Martha Matthews

Nelson became a married man for the first time at age 19. He met his first wife, Martha Matthews, after being medically discharged from the Air Force with a back injury in 1952. They wed that same year. "I was always a sucker for long-black-haired women," Nelson told Parade of Matthews, who was 16 years old when she married Nelson.

During their marriage, the couple welcomed three children together: daughters Lana and Susie and son Willie "Billy" Hugh Jr., who died on Christmas Day in 1991.

Nelson and Matthews divorced in 1962. According to the Orlando Sentinel, Matthews died in 1989 from liver failure at age 53.

Shirley Collie

In 1962, Nelson began spending time with musician and yodeler Shirley Collie, whose single "Willingly" features Nelson. A year later, they tied the knot in a 1963 wedding ceremony, however, their relationship was cut short when Collie confronted Nelson about his infidelity.

Nelson talked about his infidelities at length in his joint memoir with his sister Bobbie Nelson. In one instance, he detailed the exact moment Collie found out he had welcomed a child with another woman. "Shirley saw a bill from a Houston hospital. I tried to play it off as no big deal. I told her that I had to go to the hospital for something minor," he wrote.

"Shirley wasn't buying that for one simple reason: The bill said the charges were for the birth of a baby girl, Paula Carlene, born to a Mrs. Connie Nelson," he continued. "Shirley wanted to know who in the hell was Connie Nelson. Couldn't lie. Was caught flatfooted. Had to get the words out of my mouth. 'Connie's my girlfriend and Paula's our daughter.' "

The pair went their separate ways shortly after in 1971. Collie died in 2010; she was 78 years old.

Connie Kopeke

Nelson and Connie Kopeke first started dating while he was still married to Collie, and they welcomed a daughter together in 1969. After Nelson divorced Collie in 1971, he and Kopeke got married that same year.

The couple named their daughter Paula, who later became a big sister with the addition of their second daughter, Amy, in 1973. Their family lived a rather quiet life, though Nelson was on the cusp of making it big at that time.

Halfway into their 16-year marriage, Nelson found huge success within the movie industry. Albeit, it also led to the downfall of his third marriage. Wilson then entered into a relationship with Annie D'Angelo, a makeup artist on a film he was working on. The "Highwayman" singer continued on with the affair for two years before divorcing from Kopeke in 1988.

"I messed up another marriage. My wandering ways were too much for any woman to put up with," he wrote in his memoir. "I'll always love Connie."

Annie D'Angelo

Despite starting off hot and heavy, Nelson took things slow with Annie D'Angelo. "My love for Annie was all-consuming, but winning her over wasn't easy. She had to be sure my marriage was over and that I was truly free. She didn't care about me being a celebrity. She was whip-smart, with a keen appreciation for all forms of art. It didn't hurt that she was pretty and radiated enough energy to light up any room she entered. She also had a sharp political sense," Nelson wrote of his fourth wife in his book.

The pair first met in 1986 on the set of Stagecoach, where she was working as a makeup artist and he had been cast to portray the role of Doc Holliday. They spent the early days of their secret romance hanging out with Nelson's costars Johnny Cash, June Carter, Kris Kristofferson and Waylon Jennings.

"There was friction with my other wives. But it seems like Annie and I did okay with each other. It takes a special person to live with me," Nelson later told Parade, noting that he's "not easy to live with" and can be "pretty temperamental."

The couple welcomed sons Lukas Autrey in 1988 and Jacob "Micah" in 1990, before tying the knot in 1991. Both of Nelson's sons have followed in his musical footsteps. Lukas is the lead singer of the country rock band Luke Nelson & Promise of the Real, more commonly referred to as POTR. During the start of their career, POTR opened up for Nelson on tour. Meanwhile, Micah performs under the stage name Particle Kid.

When Nelson isn't touring, he and D'Angelo run their cannabis company, Willie's Reserve. According to the company website, they offer edibles, flowers, vape cartridges and other cannabis accessories. D'Angelo even has her own edibles line, in which she specializes in cannabis-infused chocolates.

In a May 2023 interview with PEOPLE, Nelson praised his wife for the important role she plays in his life. "I call her my pet rattler," he said. "She's my lover, my wife, nurse, doctor, bodyguard."

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