The One Direction star is known for having a way with the women and it now looks like 18-year-old Kendall has been wooed by his charm, since the pair met up for a meal in LA last night (20 November).
Fresh from a trip to New York with her older sister Kim, Kendall was back on home turf and decided to accompany Harry to Craig's Restaurant for some food.
She wore a smart grey jacket to meet up with the British singer and left her long brunette locks poker straight.
Meanwhile, Harry kept it cool and casual in a black T-shirt, which showed off his various tattoos.
The 19-year-old landed in LA earlier this week with his One Direction bandmates Niall Horan, Liam Payne, Louis Tomlinson and Zayn Malik.
But their arrival was far from low-key, since the group was instantly mobbed by a gaggle of screaming fans at the airport.
Yesterday however, Harry tried his best to remain under the radar on his rendezvous with Kendall and the pair made a quick getaway in Harry's car after finishing their meal.
Kendall - who celebrated her 18th birthday on 3 November - has been at the centre on controversy this week, after she posted a sneak peek from a photo shoot on Instagram, which showed her wearing a sheer top with no bra.
In the image the outline of the teenager's breasts can be spotted.
However, her older sister Khloe was quick to come to her defence on Tuesday night (19 November) and hit back, telling people to "enjoy the view".
Could you imagine Harry and Kendall hitting it off? Let us know below, as the best comment across the website each week wins £50!