By Michelle Tauber
March 03, 2014 12:00 PM

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BRUCE JENNER’S

SHOCKING TRANSFORMATION

AS HIS LATEST PLASTIC SURGERY SPARKS A FRENZY OF RUMORS, FRIENDS OF THE OLYMPIC LEGEND ADMIT HE’S BECOME OBSESSED WITH HIS LOOKS

FOR BRUCE JENNER THIS YEAR, Valentine’s Day was a mix of business and family. Single since his October split from his wife of 22 years, Kris Jenner, he spent part of the day filming Keeping Up with the Kardashians, the reality show in which he is an increasingly reluctant costar. Arriving alone in his Porsche, he lunched at Jinky’s Kanan Café in Agoura Hills, Calif., with stepdaughter Khloé Kardashian, 29, and daughter Kylie Jenner, 16, while E! cameras rolled. “Bruce looked happy to see the girls but didn’t seem into filming,” says a production source. After nine seasons on the show that turned his family into a multimillion-dollar brand under Kris’s firm stewardship, “Bruce has made it clear that he’ll continue filming for now, but he isn’t signing on for more,” says the production source. “He is ready to have a life outside the spotlight.”

Yet lately the 64-year-old Olympic icon’s desire to “chill out, play golf and enjoy a more low-key life,” as the source describes it, has collided with mounting interest in his dramatically altered appearance. Since the start of the new year, Jenner has sported a number of eyebrow-raising looks, including ombré-tinted hair that has grown in thickness and length, longer manicured fingernails and, most controversially, a surgically reduced Adam’s apple as a result of a “tracheal shave” procedure sometimes associated with preoperative transgender women. The changes have sparked nonstop tabloid speculation that the athlete turned reality star is transitioning toward a female identity. (One particularly blunt story alleged that Kim Kardashian feared Jenner’s “sex change” would ruin her wedding.) “Absurd,” scoffs a close family friend, one of many insiders who dismisses the rumors as false. (Jenner himself declined to comment.) “Bruce has never expressed interest in becoming a woman,” says another source close to the family. The source also refutes reports that Jenner suffers from body dysmorphia, an obsession with perceived defects in one’s physical appearance. Rather, four months after his split from Kris, 58, the father of 10 (including 4 stepchildren) “is having an identity crisis,” says the family insider. “He’s a man in personal transition.”

In more ways than one. After years of “being relegated to a corner” during his marriage to Kris – who, says the insider, was laser-focused on celebrity and often critical of her husband’s looks – “he’s breaking out of his shell a bit now.” (After their October split Kris told PEOPLE, “I do run a tight ship, but [Bruce] is no pushover!”) Since Jenner settled into his own place in Malibu last summer, his newfound independence “is liberating,” says the insider. A source close to Jenner adds, “This is what happens when, after 20-odd years, you’re finally doing whatever you want.” For Jenner that means undergoing a number of enhancements. “He wanted to grow his hair long, so he did,” says the family insider. “He wants to get manicures, so he gets them. And he’s always hated the way his Adam’s apple stuck out.”

Being on TV only exacerbated such insecurities, adds the insider: “Bruce is definitely concerned with his looks and always has been. The show made him even more hyper-aware. Certain angles make him look like he has ‘man boobs.’ He knows that and he hates it.”

But Jenner’s looks aren’t the only big change since his separation. (The two currently have no plans to divorce.) He also has been reconnecting with his children from his first two marriages: Cassandra, 33, and Burt, 35, with first wife Chrystie, and Brandon, 32, and Brody, 30, with second wife Linda Thompson. “He’s embraced his old family and friends that he hasn’t seen for years, and it’s great,” Cassandra tells PEOPLE. “My dad is really involved. He came for Christmas with presents for the kids. He’s an involved grandpa.”

As he’s grown closer to Brandon and Brody, “it just makes Bruce think he’s young and cool like them,” says the Jenner source. “He’s had a complicated relationship with them, and he’s working on repairing it.” Pursuing a youthful appearance “is a way he identifies with them.”

There is no question that Jenner’s appearance has radically changed in the years since he became one of the first superstar athletes at the 1976 Olympic Summer Games in Montreal, where he won a gold medal in the decathlon. His handsome good looks, charm and athleticism quickly landed his face on everything from Wheaties boxes to ads for shoes, clothes and cameras, boosting his net worth to an estimated $100 million. But in the mid-’80s, a not-yet-40-year-old Jenner made the surprising decision to undergo a partial face-lift and nose job. “I was just going through a bad time,” he later explained.

The subsequent scrutiny of his looks and ongoing late-night punchlines took a toll on his self-esteem, and in 2009 he went under the knife a second time to correct the first operation. “If you Google my name, [you get] the worst plastic surgeries of all time … they’ve compared me to Michael Jackson,” he said on the show. “He’s had some bad work done, and he’s been honest about trying to fix it,” says the family friend.

Friends say that Jenner’s reluctance to address the latest round of rumors is typical of a guy who values privacy far more than his estranged wife. “The reality show was not him,” says Pam Behan, a former nanny who worked for the family in the early ’90s. “He doesn’t need it. He doesn’t want it.” These days he favors quiet time on the links or flying his beloved remote-control helicopters. As for the ongoing attention, “people in the family have brought up his hair or his clothes – how absurd they think it is – but Bruce doesn’t care,” says the Jenner source. “At the end of the day, he’s happy about it,” adds the source. “Or at least trying to find what he’s happy with.”

Bruce’s Changing Looks

1976

At the Montreal Olympics, a 26-year-old Jenner took gold and the title of “world’s greatest athlete” in the decathlon.

1980

Jenner had no qualms showing off his fit physique.

1987

Jenner underwent plastic surgery in the mid-’80s. “Because you’re [an] Olympic champ, people said, ‘You shouldn’t be doing things like that,’ ” he later said.

2009

The year of his second face-lift, Jenner revealed an altered look.

Feb. 10

“It’s his life. Whatever he wants to do, he wants to do,” says daughter Cassandra Marino. “Nobody knows how it is to be in his skin.”

JEN AT 45 WHAT’S NEXT?

IF JENNIFER ANISTON IS having a hard time with getting older, she sure doesn’t act like it. On the night of her 45th birthday on Feb. 11, instead of throwing herself a pity party, she braved the throngs of paparazzi outside Soho House in West Hollywood to join a small group of friends, including Courteney Cox Arquette and hairstylist Chris McMillan, for an intimate dinner. “She looked great and seemed happy,” says an eyewitness at the exclusive club. “Fans wished her a happy birthday, and she kindly replied ‘thank you’ several times.”

Conspicuously absent: her fiancé, Justin Theroux, 42, who was in New York City shooting his new HBO series, The Leftovers. Three days later the couple spent Valentine’s Day apart too – but Aniston didn’t seem fazed. “Her attitude has always been that work is work,” says a source close to her. “Justin has always been very supportive of her career, and that’s one of the things she finds attractive about him. She would never complain that Justin was working on her birthday.”

Both of their bustling careers mean wedding plans appear to be on hold – but Aniston has plenty to celebrate. She wrapped a sequel to the hit Horrible Bosses and just signed to star in and executive-produce Cake, an indie drama about a woman who becomes fascinated by another’s suicide. “It’s a fantastic role for her,” says an industry insider. “It’s a complex character, and she’ll strike that perfect balance of drama and dark comedy.” She’s also shot new campaigns for her lucrative Aveeno and Living Proof endorsements, and the night before her birthday joined influential women including Martha Stewart and Gloria Steinem at the MAKERS Conference outside L.A. When Aniston noted that women are often judged by their “marital status or if we’ve procreated,” Steinem replied, “Well, I guess we’re in deep s–t!” Aniston laughed and agreed—and for now she’s still laughing off the speculation that swirls around her. “Only time will tell what will happen,” says the source close to her, “but Jen seems very happy right now.”

A Birthday Apart

Boys’ Night

Shooting in New York, Justin Theroux kicked back with pal Orlando Bloom on Aniston’s Feb. 11 birthday at a party for biker-wear label Deth Killers of Bushwick.

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