Kerry Kennedy had always been clear that she’d never endure the sorts of unhappy marriages she’d seen all around her from the time she was a child. A romantic at heart, she always felt she’d be one day swept away by someone like her father and have a storybook romance like her mother’s. “I envy your beautiful memories of Daddy,” she once told her. She’d been engaged to a young man in college, someone for whom she fell hard. Tragically, he had a heart attack and died while having a snowball fight. It was devastating. Therefore, at the time she met Andrew, in 1989, Kerry was fragile. He helped heal her heart. He was warm and open, from a family that reminded her of the closeness of her own. Friends would note that when he looked at Kerry it was as if he were gazing at an apparition; he seemed to not believe his good luck in finding and then falling for her. He proposed on Valentine’s Day 1990.
“When the engagement was announced, the media was giddy with anticipation about the melding of these two powerful political families,” legendary White House reporter Helen Thomas recalled in a 1999 interview. “The usually staid New York Times wrote something like ‘This story has just about everything: love, politics, history’ … the whole shebang. There actually were some similarities between the two families: both hailing from immigrants—Ireland and Italy—both beginning journeys as underdogs in America, gaining money, power, and influence along the way, and then using it to do battle on the political landscape. But the Kennedys had so much more clout than the Cuomos on a national stage. I think some of them wondered why the heck they were even being compared to the Cuomos. They considered themselves so much more of a dynasty with so many more political power brokers. Andrew’s father, Mario, had long been in Democratic politics; he’d served as the fifty-second governor of New York for three terms, from 1983 to 1994. So the Cuomos basically just had him at the top of the family tree and Andrew on the next limb down. Still, when he and Kerry married, a lot of people looked at it as the merger of two political powerhouse families.”
Some reports had it that the Cuomos hoped that being linked with the Kennedys would advance Andrew’s political aspirations. However, because of the scandals that had long been a hallmark of Kennedy history, Mario wasn’t sure that aligning with the beleaguered family would do him or his son much good. “We don’t engage in scandal” is how Andrew put it. “That’s not who we are.”
The Kennedys would soon learn that Andrew wasn’t necessarily a lighthearted person; many people found him to be downright humorless. What had always been true about the Kennedys was that, despite any problems, they liked to have fun. In that respect, Andrew didn’t fit in with them. When he was with his brothers-in-law either at Hickory Hill or at the compound, he wanted to discuss policy, while they wanted to play football. For them, policy was dinner-table conversation, not really for the outdoors. However, even in that dining arena, Andrew didn’t seem to blend in. He was never able to squeeze in a word between the many viewpoints, opinions, and criticisms. He actually began to not enjoy being around the Kennedys. That was fine with Kerry, at least at first. She’d had enough of her family anyway and was eager to get to know his. Typical of their differences, when the families began to plan the wedding, Andrew said he didn’t want any toasts to be offered at the reception. This took the Kennedys by surprise; the giving of a toast was a family tradition at any gathering, big or small. However, Andrew was worried about what the Kennedys might say that would embarrass him or his relatives.
There were probably going to be familial differences no matter who it was Kerry married; she was experienced enough in life to make up her own mind about things. She married Andrew on June 9, 1990, at St. Matthew’s Cathedral in Washington, D.C. The couple then moved into Hickory Hill while they searched for a home in Queens at about the same time that Andrew got a top cabinet position as an assistant secretary of HUD. Living in his mother-in-law’s manse would definitely not be easy, though.