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  1. 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.

  2. 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”. Shooter’s full name is “Waylon Albright ...

  3. In 1997, de Matteo opened Filth Mart, a clothing store with her then-boyfriend Michael Sportes. They closed the store in 2004. 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.

  4. "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 37-year-old actress ...

  5. 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 ...

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  7. Nov 29, 2007 · Shooter Jennings and longtime girlfriend Drea de Matteo welcomed a baby girl on Wednesday night (Nov. 28) in New York. They named her Alabama Gypsy Rose. She weighed 8 pounds, 3 ounces. Jennings ...

  8. Nov 29, 2007 · Published on November 29, 2007 04:15PM EST. Former Sopranos star Drea de Matteo has given birth to a baby girl, Alabama Gypsyrose. The actress, 35, and musician boyfriend Shooter Jennings, 28 ...

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