Paul McCartney Engaged to Nancy Shevell: Third Time Charmed?

May 10, 2011— -- Many thought Paul McCartney would never marry again, following his bitter divorce from second wife Heather Mills, to whom the famously frugal Beatles singer had to fork over a reported $35 million.

But it turns out the 68-year-old McCartney is still a romantic at heart. Last weekend he proposed to New York businesswoman Nancy Shevell, 51, whom he has quietly dated for four years, with a vintage 1925 Cartier solitaire diamond engagement ring worth a reported $650,000. Moreover, he has reportedly rebuffed a prenuptial agreement.

The latter is seen as a sign of McCartney's trust in Shevell, who has more in common with McCartney's first wife, Linda, who died of breast cancer at age 56 in April 1998, than his infamous ex, Mills.

Says Popeater's Rob Shuter, "She's with him for all the right reasons."

So, who is this woman who has quietly captured McCartney's heart? Some details on Shevell and how she stacks up to McCartney's previous wives:

She Has Her Own Money

"She's a very, very different lady than Heather Mills," Shuter told ABCNews.com. "She's incredibly wealthy and successful in her own right."

Shevell is the daughter of Mike Shevell, whose transportation conglomerate is reportedly worth nearly a half billion dollars. Nancy Shevell is the company's vice president and a board member of the Metropolitan Transportation Authority.

She told New York Post gossip columnist Cindy Adams that though she'll likely live in England with McCartney, "I still have a job here so I'll commute once a month."

Shevell's own wealth is only part of the reason why McCartney is eschewing a prenup, Shuter said. "Paul is saying, 'This girl is not Heather,'" he said. "He changed Heather's life financially. She went from regular girl to very wealthy.

According to London's Daily Mail, McCartney's lawyers have drawn up a one-page document in which Shevell agrees not to go after the trust funds of any of McCartney's children -- he had four with Linda, and a daughter, Beatrice, with Mills -- should the new marriage fail.

But friends of the former Beatle say he intends to grow old with Shevell.

She's an Old Friend

Shevell and McCartney first met 20 years ago in the Hamptons, on New York's Long Island, where they both had homes. Shevell, a cousin of ABC News' Barbara Walters, was married to Bruce Blakeman, a Nassau County lawyer and sometime politician, with whom she has a son, Arlen, who is now in college.

The Blakemans and McCartney's socialized together and, according to the Daily Mail, his children even nicknamed her Jackie O for her sense of style and love of sunglasses. Shevell and Linda McCartney shared more than friendship -- both had breast cancer around the same time.

Shuter said there are many similarities between the two women. "She's a lot like the Linda toward the end of her life than the one Paul fell in love with," he said.

"Nancy is fancier than Linda," Shuter said. "She's a lot more of a businesswoman. She comes with all the skills that Linda had to learn and Heather never learned."

The Daily Mail says McCartney and Shevell's romance began with a couple low-key meetings during the summer of 2007, a few months after his separation from Mills. Shevell had also separated from her husband. Her divorce was completed Dec. 9, 2008.

Within 12 months, Shevell and McCartney were nearly inseparable. According to the Mail, she even adopted his vegetarian lifestyle. The Post's Adams says Shevell always accompanies McCartney on his travels because he doesn't like to be alone.

She Shuns the Spotlight

Like Linda McCartney and unlike Mills, Shevell prefers not to be in the spotlight. "She is terribly private and discreet," Shuter said. "I've seen her with Paul at different events, and she really doesn't want to be photographed. She'd rather be in the shadows."

Mills, on the other hand, was a model and actress and had once posed for nude photos. "Nancy is not as bubbly or full of life as Heather was," Shuter said. "But she comes with a lot fewer problems."

Mills opted for a lavish wedding in a castle in Ireland, while Shevell is planning a family-only affair in the backyard of her Hamptons home this summer.

She's Got Stella's Approval

Speaking of family, Shevell has apparently earned the stamp of approval from McCartney's fashion designer, daughter Stella.

"We all know that Stella hated Heather," Shuter said.

And according to the Daily Mail, Stella was initially resistant to the idea of McCartney getting married again but has since come around.

"She considers Nancy to be a solid woman," Shuter said.

It doesn't hurt that Shevell wears a lot of Stella's designs and was photographed last weekend flashing the designer's latest handbag -- and her engagment ring.