After defeating cancer and winning the Tour de France seven years in a row, Lance Armstrong is tackling a new challenge: a fifteen-year age gap between him and new fling Ashley Olsen.

The new couple was spotted at New York hotspot Rose Bar on October 29 by an eyewitness who tells Us Weekly, “they were being very flirtatious.” The next night, the May-December duo took in Broadway play Young Frankenstein before dinner and wine at the Waverly Inn.

And while Armstrong prepped to run last Sunday’s New York City Marathon, the lovebirds shacked up at luxe hotel Soho House, where they both had booked rooms.

Sources tell Us, however, that Olsen shouldn’t let herself get swept away by the whirlwind Big Apple romance. “Lance is a candidate for a midlife crisis,” says a source close to the divorced father of three.

Indeed, Armstrong might already be in his midlife crisis: he recently split from fashion designer Tory Burch and broke off his engagement with Sheryl Crow in 2006. “Next week, he’ll be on to someone else,” another insider says.

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Jake Gyllenhaal and Lance Armstrong are hanging at the Tour De France together because the actor is the leading contender to play the cyclist in a Sony bio pic being quietly developed.

On Sunday, the two sat in a Paris hotel together with friends as American Floyd Landis stood on the podium after winning the 2006 Tour de France. Needless to say, the European press went into a speculation frenzy when the Lance and Jake first showed up together .

As Saturday’s all-important Individual Time Trial began, Jake joined the seven-time TdF winner in the Discovery team car for a ride-along as Lance protégé Yaroslav Popovych pedalled away. (Lance’s Discovery team faltered without him this TdF, but Landis of Phonak took the yellow jersey and eventually won the overall race). Earlier in the day, Lance met with the Tour de France organizers to lessen the tension.

Armstrong, his agent Bill Stapleton, Discovery sports manager Johan Bruyneel, and Tour de France Directors Jean Marie Blanc and Christian Prudhomme had what insiders called “a heart-to-heart discussion” aboard the Discovery bus. “The meeting went well,” Bill Stapleton said later. “Everyone left with a feeling of mutual respect.” Obviously the Tour’s assistance, while not required, would be helpful to the bio-pic. Gyllenhaal and Armstrong have become pals during Jake’s method process to get to know the sports legend.

The actor of Brokeback Mountain and Jarhead fame is even a long-time cyclist and has begun training for the film. Armstrong is no stranger to Hollywood: Robin Williams used to join Lance in the Alps while Armstrong was defending his Tour titles. And Armstrong hangs with Matthew McConaughey whenever the cyclist is in Los Angeles. Also, while they were together, Lance and Sheryl Crow were fixtures on the Hollywood charity and awards circuit.