Relive Harry Styles' Star-Studded Dating History, From Taylor Swift to Kendall Jenner

Sometimes, it seems like just yesterday that Kendall Jenner was a shy teenager on Keeping Up with the Kardashians.

It pays to be a social media queen… literally. A new list by Buzz Bingo showed who were the top Instagram earners in 2019 and Kendall Jenner, 24, takes the cake by being the highest paid female Instagram personality and third overall with $15.9 million.

The annual Kardashian Christmas Eve party tradition continued this year, with Kourtney Kardashian taking on hosting duties. All the sisters were there, and the youngest girls—Kylie and Kendall Jenner—came dressed in the most glam holiday party ensembles imaginable.

It looks like Kendall Jenner and not Kylie Jenner will be topping the list of Instagram’s highest earning women this year, as the supermodel, 24, is revealed as the highest ranking female on the list of the year’s biggest social media money-makers. A list, compiled by Buzzbingo.com , puts the stunning model at a fortune of around £12.7 million from Instagram over the last 12 months, which is four times more than her younger sister Kylie.

Joe Alwyn and Taylor Swift have spent the last three years only talking about why they don’t talk about their relationship in interviews if they’re ever asked about it. But Alwyn actually said a few words about the Taylor Swift boyfriend experience in his new The Times interview.

Kendall Jenner isn't just making visits to Philadelphia to figure out where her relationship with NBA player and on-off boyfriend Ben Simmons stands, E! reports. They're actually dating again, but they're being very low-key about it.

Harry Styles, 25, appeared a bit caught off guard when Ellen DeGeneres, 61, asked about the status of his relationship with supermodel Kendall Jenner, 24, on the Dec. 18 episode of Ellen. “So when you hosted [The Late Late Show] for James Corden, your guests were Tracee Ellis Ross and Kendall Jenner,” Ellen began before asking, “And you and Kendall are really good friends now, right?” Harry, being as modest as he could be, scratched his leg before offering his answer.

Ellen DeGeneres did not make things easy for her guest Harry Styles. In addition to asking point-blank whether his new album Fine Line was inspired by a breakup (his with Camille Rowe, although she didn't name names), she also let the interview get pretty awkward when talking about his other ex-girlfriend Kendall Jenner.

Harry Styles and Kendall Jenner are the definition of amicable exes.

Harry Styles may be on good terms with his ex Kendall Jenner, but he still had an adorably awkward reaction after Ellen DeGeneres brought up the model in a new interview.

Harry Styles isn't interested in spilling about his personal life, not even to Ellen DeGeneres! The 25-year-old former boy bander has been linked to stars like Taylor Swift and Kendall Jenner, but he doesn't seem particularly keen on dishing about the rumored romances, no matter how many hints are thrown out. 

Remember the other day when Kendall Jenner randomly showed up on The Late Late Show with her ex-boyfriend Harry Styles and they ate cod sperm and bull penis together? Good times, good times. During the hang, , and she fully ranked Kourtney Kardashian worst. Direct quote: "it would be like, Khloe, Kim, Kylie, Kourtney."

You should have filled your guts, Kendall Jenner!

Tensions have been high between Kourtney Kardashian and the rest of the Kardashian-Jenner family. So it didn't help things when Kendall Jenner appeared on last week with guest host and her rumored ex, Harry Styles, where she played a headline-making game of «Spill Your Guts or Fill Your Guts.» During the game, Kendall ranked her siblings from best to worst parent, putting Rob Kardashian as the best and placing Kourtney as the worst. 

‘Tis the season to have boundaries! Kim, Khloé and Kourtney Kardashian joined their mom, Kris Jenner, and half-sister Kendall Jenner on a family vacation in Jackson Hole, Wyoming, on the Sunday, December 15 season finale of Keeping Up With the Kardashians.

Getting territorial? Kendall Jenner teased her little sister, Kylie Jenner, after the makeup mogul posted photos with the model’s close friend Fai Khadra.

Uh-oh...