Jennifer Graylock/JPI; Jeff Vespa/Wireimage
Lance Armstrong and Ashley Olsen
appear to be getting friendly: The unlikely twosome have met up at least twice this week while the former Tour de France champ is in town for the New York Marathon, sources tell PEOPLE.
The pair first shared a special moment on Monday night, getting close at the Rose Bar inside the Gramercy Park Hotel. (The rendezvous was well-documented in New York's newspapers
An observer tells PEOPLE: "Lance was hanging with her, definitely. [Olsen] was very flirtatious, and was sitting on his lap."
Another source said Olsen was with a group and "hanging out, having a good time."
Armstrong, 36, and Olsen, 21, reunited again in the wee hours Wednesday at hip restaurant the Waverly Inn. (Armstrong was there earlier that evening with Texas pal Owen Wilson
The retired cyclist and fashion designer Tory Burch recently broke up
after a year-long relationship. A rep for Armstrong had no comment.
By TIFFANY MCGEE, ALYSSA SHELASKY, JEFFREY SLONIM, TIM NUDD and LESLEY MESSER