The musician also tweeted about popping the question. "Asked Drea to marry me on stage tonight. I'm a lucky man. I'll never forget Utica," he wrote.
Jennings, 30, and de Matteo, 37, have been dating since 2001. They had a daughter in 2007.
In addition to her role as The Sopranos' Adriana La Cerva, de Matteo also starred in the Friends spin-off Joey and has appeared on Sons of Anarchy. Her next slate of projects includes New York, I Love You, which also features Blake Lively and The Hangover's Bradley Cooper, among other stars.
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