Conor — who just turned 18 last week — has been quietly wooing the 22-year-old pop country singer for nearly a month and the two have been spotted all over Westchester County in New York and the Kennedy compound in Massachusetts.
"I was out to lunch with a few friends in Mount Kisco and as we're walking down the street from the diner, we see Conor Kennedy emerge from a pizza shop with Taylor Swift right behind him," eyewitness Jeff L. exclusively told RadarOnline.com.
"They were holding hands and both had huge grins on their faces. Taylor playfully leaned into him as they walked."
And as Star magazine was first to report, Taylor's parents are separating after nearly 25 years of marriage, leaving both her and Conor with broken families and tragic times that one source says may be what is bonding the two young lovebirds.
"Conor and Taylor actually have a lot in common and can really relate to each other," an insider said.
"And Conor is set to inherit his mother's fortune and oversee her estate now that he's a legal adult, which is very appealing to Taylor because she sees him as more of a man now and she needs that stability in her life."
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