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Jennings began dating actress Drea de Matteo in 2001. They have two children together, a daughter born in 2007 [30] and a son born in 2011. [31] Jennings and de Matteo eventually ended their relationship without marrying.
Apr 7, 2011 · Shooter Jennings, son of country music Outlaw legend Waylon Jennings, 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.
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.
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.
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Jun 15, 2009 · Silverman says Jennings took de Matteo by surprise when he called her to the stage to pop the question. The couple have an 18-month-old daughter, Alabama. In an update on Twitter, Jennings...
May 15, 2007 · Shooter Jennings' longtime girlfriend, actress Drea de Matteo, is pregnant with her first child, her publicist confirmed Tuesday (May 15) to The Associated Press.
