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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 on Wednesday.)
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
