The One Direction heartthrob and Keeping Up with the Kardashians star are rumoured to be dating after they were seen together several times last year.
The 19-year-old singer is apparently extremely keen on model Kendall, so is preparing to go all out to impress her this year.
“Harry’s really keen on Kendall, so it planning a series of activity dates in 2014,” an insider told British magazine Heat.
It seems Harry has already put his plan into action as the pair were seen enjoying a ski break over the festive season.
The couple hit the slopes with friends in Mammoth, California, with Harry seen gazing adoringly at his model love interest and Kendall glancing around with a coy smile on her face.
The One Direction star has even started probing his supposed girlfriend for tips on how to impress her.
“He asked Kendall, 18, what she’d most like to do when he was back in America and she said horse riding,” the source explained. “She told him she adores horses and has been riding for ten years and if she wasn’t so busy with her fashion career she’d be riding all the time.”
Neither Kendall nor Harry have confirmed they are dating, with Kendall insisting they were just good friends last year. However, things are now said to have moved on and Harry has even met her father Bruce Jenner.
“When Harry and Bruce met at his Malibu home a couple of weeks ago, Harry charmed his way through the visit by talking about golf.
Bruce is very protective when it comes to his daughters,” a source told British newspaper The Daily Star earlier this month.
“He’s experienced how difficult it’s been to have a relationship in the public eye with his estranged wife Kris. Harry wasn’t in for an easy ride but things couldn’t have gone better, all thanks to golf.”
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'Finesse' Joseph Young is a Model, Fashion Stylist, TV Host, Blogger, Social Media Strategist, Online & TV Personality. Modelsvillage.tv once said 'He's arguably one of the most followed Nigerian Models on Twitter & Instagram.'
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