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  2. Jennings began dating actress Drea de Matteo in 2001. They have two children together, a daughter born in 2007 and a son born in 2011. Jennings and de Matteo eventually ended their relationship without marrying. Jennings married long-time friend Misty Brooke Swain on June 4, 2013, in Joshua Tree, California.

  3. De Matteo started dating musician Shooter Jennings in 2001. They became engaged on June 11, 2009, when Jennings proposed onstage at the Stanley Theater during a show in Utica, New York. They have two children together. Jennings and de Matteo eventually ended their relationship without marrying.

  4. Apr 7, 2011 · Shooter Jennings, son of country music Outlaw legend Waylon Jennings and Jessi Colter, along with his long-time partner and fiance, Drea De Matteo, most famous as “Adriana” from The Sopranos, have given birth to a baby boy with a famous first name: “Waylon Albert “Blackjack” Jennings”.

  5. Jun 6, 2013 · Previously, Jennings dated actress Drea de Matteo, fathering two children with her. Alabama Gypsy Rose was born in November 2007 and Waylon Albert "Blackjack" Jennings was born in April...

  6. "Sopranos" star Drea de Matteo and her longtime boyfriend, country singer Shooter Jennings, are engaged.Amanda Silverman, publicist for de Matteo, says Jennings proposed to the...

  7. Jun 12, 2009 · Drea de Matteo and her longtime boyfriend Shooter Jennings got engaged Thursday night at the rocker’s concert in Utica, N.Y., PEOPLE has confirmed. “ [Drea] was dancing on the side of the...

  8. Mar 4, 2024 · Drea de Matteos relationship with Shooter Jennings, characterized by its highs and lows, offers a glimpse into the complexities of love in the public eye. The talented actress later moved on and, in July 2015, announced her engagement to Michael Devin, the bass guitarist for the band Whitesnake.

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