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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. 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.

  3. Apr 27, 2023 · While Drea de Matteo had been in a relationship with musician Shooter Jennings since 2001, the two didn’t become engaged until 2009 when she said yes live on stage at one of his concerts. The couple would welcome two children together, seemingly taking their names from an Old West-themed Madlibs book before eventually falling out of love and ...

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  5. "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...

  6. Jun 15, 2009 · NEW YORK — “Sopranos” star Drea de Matteo and her longtime boyfriend, country singer Shooter Jennings, are engaged. Amanda Silverman, publicist for de Matteo, says Jennings proposed...

  7. Feb 2, 2008 · Actress Drea de Matteo, 35, and her rocker boyfriend Shooter Jennings, 28, (neither pictured) were snapped stopping at a Babies R Us in Los Angeles on January 24th to pick up some nursing...

  8. Apr 8, 2011 · The late legend's son's full name is Waylon Albright "Shooter" Jennings. Blackjack is the second child for Jennings and de Matteo, who have a 3-year-old daughter, Alabama Gypsy Rose. Filed Under ...