Tiffany Trump appears to be dating a fellow UPenn'er named Ross Mechanic if we go by her Instagram account. Tiffany Trump is pictured here at the VH1 Save The Music Foundation's "Hamptons Live" benefit hosted by Billy and Julie Macklowe at a private estate in Sagaponack, NY on August 8, 2015. (Photo by Matthew Eisman/Getty Images for Vh1 Save The Music)
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