They say love deserves a second chance. But in Hollywood, second chances don’t always lead to happy endings.
Some celebrity couples broke up, made up, and even walked down the aisle—only to find out round two was worse than the first.
Whether it was old issues coming back, fame pressure, or just poor timing, these stars gave love another shot and later wished they hadn’t.
Here are 11 celebrities who married their ex—and regretted it big time.
1. Elizabeth Taylor and Richard Burton Elizabeth Taylor and Richard Burton’s love story was passionate—and chaotic. They married in 1964 after falling in love on the set of Cleopatra.
Their fights were as famous as their romance. They divorced in 1974 but couldn’t stay apart. Just 16 months later, they remarried. Sadly, the second try only lasted nine months.
Taylor later said their love was too intense to survive. Their second marriage ended in more heartbreak, proving some flames are better left in the past.
2. Eminem and Kim Scott Eminem and Kim Scott had a relationship filled with drama. They first married in 1999 and divorced in 2001.
Despite their messy history, they gave it another try in 2006. But it didn’t last. They divorced again just months later.
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Eminem has often talked about the pain in his songs. He admitted later that remarrying wasn’t the best decision.
The love was real, but the wounds were too deep.
3. Melanie Griffith and Don Johnson Melanie and Don first tied the knot in 1976, but the marriage lasted only six months. Still, they stayed close and remarried in 1989 after reconnecting.
This time, they had a daughter, Dakota Johnson. But even with a family, their second marriage ended in 1996. Melanie later admitted they were better as friends than spouses.
Their bond remains, but both have said that getting remarried brought back the same problems.
4. Pamela Anderson and Rick Salomon Pamela and Rick’s relationship was a wild ride. They first married in 2007 but annulled it just two months later. Shockingly, they remarried in 2014.
That reunion didn’t last either. They filed for divorce again within a year. Pamela later described the whole thing as a “bad habit.”
She said marrying the same person twice was a mistake she wouldn’t repeat.
5. Jean-Claude Van Damme and Gladys Portugues Action star Jean-Claude Van Damme married Gladys Portugues in 1987. They divorced in 1992, but by 1999, they had remarried.
At first, it seemed like things had improved. But in 2015, Gladys filed for divorce again. Though they called it off that time, their marriage has been on shaky ground.
Van Damme admitted their issues never truly went away. Getting back together may have brought comfort—but also old pain.
6. NeNe Leakes and Gregg Leakes Reality TV fans watched NeNe and Gregg Leakes’ ups and downs on The Real Housewives of Atlanta. They divorced in 2011 after 14 years together.
But just two years later, they got remarried in a televised ceremony. Sadly, things weren’t smooth the second time either. Gregg’s health battles and NeNe’s rising fame added pressure.
Though they stayed together until Gregg’s passing in 2021, NeNe has admitted their second marriage wasn’t easy.
7. Larry King and Alene Akins Larry King married Alene Akins twice—first in 1961 and again in 1967. They had a son together and tried to make it work.
But both marriages ended in divorce. Larry was known for his many marriages, but this double attempt stood out.
He later said he wasn’t cut out for long-term love. Marrying Alene twice didn’t change that.
8. Richard Pryor and Jennifer Lee Comedian Richard Pryor had a famously chaotic love life. He married Jennifer Lee in 1981. They divorced in 1982 but remarried in 2001.
His health declined in later years, and Jennifer stayed by his side.
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Still, their second marriage wasn’t peaceful. Jennifer later revealed the same old arguments resurfaced.
Though she stayed with him until his death, she admitted that remarriage brought more challenges than closure.
9. Marie Osmond and Stephen Craig Marie Osmond first married basketball player Stephen Craig in 1982. They divorced in 1985. But after decades apart and raising kids with other partners, they reconnected.
In 2011, they got remarried. Marie said it felt right—but others close to her weren’t so sure. While they remain together, Marie has admitted their early problems weren’t entirely gone.
Some fans feel she might’ve rushed into round two with rose-colored glasses.
10. Sinbad and Meredith Adkins Comedian Sinbad married Meredith Adkins in 1985. They divorced in 1992 but remarried in 2002. Since then, they’ve remained together.
But Sinbad has joked about the ups and downs in interviews. He once said getting remarried felt like buying the same car again—hoping it runs better this time.
Despite sticking it out, the couple admits it hasn’t been easy.
11. Frida Kahlo and Diego Rivera This artistic power couple first married in 1929. Their relationship was full of passion and betrayal. They divorced in 1939—but couldn’t stay apart.
A year later, they remarried. The second marriage had strict rules, including no physical intimacy. Still, their emotional bond was strong. Frida later expressed regrets about their second union.
It brought stability but not happiness. Their story shows that even intense love isn’t always enough.
Giving love another chance is brave. But for these celebrities, it didn’t always lead to a fairytale ending.
From emotional chaos to repeating old mistakes, they learned that some relationships are better left in the past.
While fans hoped for lasting love, these stars discovered that sometimes, moving on is the real happy ending.
