The 32-year-old divorcing dad was spotted snuggling up to and laying some smooches on the 22-year-old daughter of his ex-wife's tummy tuck surgeon during a nighttime horse-and-carriage ride through New York City Saturday night, according to Usmagazine.com.
The PDA-heavy pair then dined at the Oak Room in The Plaza Hotel, the magazine reported.
On Sunday, the couple took a romantic stroll in the rain through the city.
Gosselin was spotted with Glassman a day after he was slapped with a lawsuit by TLC, who said Jon was in breach of his contract for "Jon & Kate Plus 8." The ex-reality TV star had previously halted filming of his eight kids.