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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. 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”.

  4. 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.

  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...

  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. Jan 26, 2011 · Baby bump debut! An expectant Drea de Matteo and Shooter Jennings take daughter Alabama Gypsyrose, 3, to Disney on Ice ‘s Princess Wishes opening night, held Friday at Madison Square...

  8. Apr 8, 2011 · 2:56 PM. Shooter Jennings and actress Drea de Matteo have welcomed their second child, a son named Waylon Albert "Blackjack" Jennings. The musician sent a note on Twitter on Thursday...

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