That's a lot to invest in an institution that Chelsea's father so famously tarnished. But experts say that watching her parents work through their own problems might have given her a better chance at achieving marital bliss.
"I think Chelsea is amazingly grounded. She's maintained a very quiet, private life that's very successful," said Jeanie Snodgrass Almo, who went to high school in Chicago with Hillary Clinton and kept in touch with the current secretary of state until a move to Philadelphia in 1999.
These days, Almo is a psychotherapist and the founder of her own practice, Fairmount Associates on Brown Street.
Marital problems in general take a tough toll on kids, Almo said - not to mention the added pain of the media circus that surrounded Bill Clinton's affair with White House intern Monica Lewinsky.
"I think kids can either be burned by their parents' experiences or I think they can grow from it," Almo said.
But the Clintons' obvious love for Chelsea could have kept her sane. "I don't think Chelsea ever doubted that both of her parents adored her and supported her."
That said, someone who has witnessed such pain between her parents likely would take precautionary measures and establish some ground rules for her spouse-to-be, Almo said.
"I would imagine that she and he would have talked very clearly about what they do and don't want," she said. "Chelsea's a smart gal. ... I think she will probably be clear on what she expects."
Mezvinsky, who grew up on the Main Line, is no stranger to very public scandal, either. His father, Ed Mezvinsky, a former U.S. representative from Iowa, pleaded guilty in 2002 to cheating dozens of investors out of $10 million. And in the midst of the scandal, the senior Mezvinsky divorced his wife, former U.S. Rep. Marjorie Margolies-Mezvinsky, who represented Montgomery County.