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Drea de Matteo | Source: Getty Images
Drea de Matteo | Source: Getty Images

Drea de Matteo's Dating History Includes Several Musicians

Christell Fatima M. Tudtud
Mar 16, 2023
09:15 P.M.

The famous actress Drea de Matteo has achieved many great things and has a high status in Hollywood. Her success has made her loyal fans wonder if she is married or has a husband.

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Even though Drea de Matteo's acting skills have wowed audiences in both movies and TV shows, her personal life is a constant source of interest for her loyal fans.

Having a romantic past mostly centered around rock and roll, the skilled actress has dated several musicians, among them the son of a renowned music legend.

Drea de Matteo attends the 2019 MTV Video Music Awards at Prudential Center on August 26, 2019, in Newark, New Jersey. | Source: Getty Images

Drea de Matteo attends the 2019 MTV Video Music Awards at Prudential Center on August 26, 2019, in Newark, New Jersey. | Source: Getty Images

Drea de Matteo has gained recognition for her versatile performances on-screen. Her breakout role was in the acclaimed drama series "The Sopranos," which mainly starred James Gandolfini and Michael Imperioli.

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She also stunned fans with her acting in the series "Desperate Housewives," Since then, De Matteo has continued to wow audiences with her acting, appearing in various films and TV shows such as "Made," "Swordfish," and "Deuces Wild."

However, being a celebrity also entails de Matteo's personal life under constant public scrutiny. Even so, she is still a respected and loved figure in the industry, known for her continuous hard work and exceptional talent.

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Michael Devin Proposed to Drea de Matteo Onstage in 2015

In 2015, de Matteo experienced a magical moment when her then-boyfriend, Michael Devin, the bassist of the rock band Whitesnake, proposed to her romantically. A fan recorded the sweet gesture during the band's Atlantic City, New Jersey concert.

Devin had been in love with de Matteo since they first met, and he took the opportunity to profess his love to her in front of a cheering crowd. He held nothing back and wanted to embarrass her as much as possible.

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The rock star called de Matteo's attention. She then came on stage with her two children and approached him. Devin picked up de Matteo's son, held him in one arm, and asked her:

"I have two questions for you: One, will you make sweet passionate love to me for the rest of my life?"

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The crowd erupted in excitement. Devin's gesture moved de Matteo, who responded, "Forevermore." She then asked Devin if he would love her children forevermore, to which he replied with a "yes."

The stunning actress appears to be dating a musician from the band UVWAYS, reportedly named Robby Staebler.

Michael Devin and Drea de Matteo attend the 2017 Rhonda's Kiss Benefit Concert at Hollywood Palladium on December 8, 2017, in Los Angeles, California. | Source: Getty Images

Michael Devin and Drea de Matteo attend the 2017 Rhonda's Kiss Benefit Concert at Hollywood Palladium on December 8, 2017, in Los Angeles, California. | Source: Getty Images

Drea de Matteo Had a Relationship with Shooter Jennings and They Share Kids

It wasn't the first time de Matteo had been proposed to on stage. Before Devin, her ex-boyfriend, musician and late singer Waylon Jennings' son, Shooter Jennings, had also made the same gesture.

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Although de Matteo and Jennings are no longer together, they share two children: son Waylon Albert and daughter Alabama Gypsy. Some Instagram posts indicate that they share a common affection for their kids.

During Waylon's ninth birthday in 2020, de Matteo fondly called him the "man of my "dreams." Jennings remarked Waylon was his "little wingman." The proud dad also noted that he was a "born leader with a sense of humor" and the "coolest guy."

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When their daughter Alabama turned 13, Jennings described her as a "little kind, soulful, brilliant, beautiful, artistic dreamer." He said he was lucky to be called her daddy. De Matteo simply stated: "13 years of Magickkkkk."

Since the couple's split, little is known about Jennings' dating life. However, a recent February 2023 post suggested he had found a new woman, named Misty Brooke. Similarly, de Matteo also found her match.

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Drea Seems to Be in a New Relationship with Another Musician

The stunning actress appears to be dating a musician from the band UVWAYS, reportedly named Robby Staebler. The couple has been sharing affectionate photos and videos on Instagram.

Recently, de Matteo posted a birthday message for Staebler, expressing her gratitude for having him in her life. She noted him as "the best beast of a man."

In 2022, she shared a video compilation of pictures in honor of Staebler's special day. The clip featured the couple's precious moments together and Staebler's fun moments with de Matteo's kids.

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Staebler, for his part, has publicly expressed his affection for de Matteo. He sent her a sweet birthday greeting with a beautiful picture of de Matteo and called her a "magic mama."

Meanwhile, de Matteo uploaded an adorable picture of her and her daughter hugging Staebler and an artistic snap of the two lovebirds on the sidewalk. She simply captioned each photo with heart emojis.

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