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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.
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.
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...
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”.
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.
Jun 13, 2009 · Drea de Matteo and boyfriend Shooter Jennings are ready to tie the knot. Just ask anyone who was in attendance at Jennings' Thursday-night concert. Jennings — a music artist and son of...
Jun 15, 2009 · "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...
