Join or Sign In

Sign in to customize your TV listings

Continue with Facebook Continue with email

By joining TV Guide, you agree to our Terms of Use and acknowledge the data practices in our Privacy Policy.

The most stylish sisters on the scene have been tied to a few high-profile bad boys. Some are confirmed, others are just all kinds of speculation.

lisa vecchione
tvgjennerloveskylietyga.jpg
1 of 12 Splash

1. Kylie & Tyga

It's a pretty sure bet that the relationship between Kylie and Tyga is a real one. Comments from stars like Kanye West and even Caitlyn Jenner all but verify that the two are official. To celebrate Kylie turning 18 (and therefore legal), the 25-year-old rapper gifted her a blowout party, complete with a new Ferrari.

2 of 12 Zhou junxiang, © Imaginechina/Corbis

2. Kendall & Chris Brown

The stylish sisters have been tied to a few high-profile bad boys. Some are confirmed, others are just all kinds of speculation, like this one.

According to reports, the two dated or have been dating for months. According to other reports, they're just friends, but a cozy Instagram photo featuring the two celebs was perhaps the final straw for Brown's relationship with Karrueche Tran.

3 of 12 Corbis, Splash

3. Kendall & Harry Styles

It's no secret that Kendall has said that she and Harry Styles are "meant to be together."

In March of 2016, Kendall's squad-sister Selena Gomez told the press that she's the only single lady in her crew, which leads us to believe that Kendall is dating someone. Most likely Harry Styles, but perhaps Chris Brown.

4 of 12 Splash

4. Kylie & Jaden Smith

Sharing in the name of sisterly love? Though Jaden was first tied to Kendall, the rumor that he and Kylie were dating went into hyperdrive following the pair's kiss in Smith's "Blue Ocean" video.

5 of 12 Corbis

5. Kendall & Justin Bieber

Kendall may have a thing for a man with a smooth voice. In the past, she was seen partying and carrying on with the Biebs.

6 of 12 Corbis

6. Kylie & Cody Simpson

Before talk started about Jaden Smith, Kylie dated this Australian singer.

7 of 12 Splash

7. Kendall & Ashton Irwin

Yet another singing sweetheart, 5 Seconds of Summer star Irwin has been linked to Kendall. Okay, he's not such a "bad" boy, but those boy band members are always up to some shenanigans.

8 of 12 Splash, Corbis

8. Kylie & Justin Bieber

Another instance where both sisters were linked to the same playboy. Not sure if we're Beliebing it, though.

9 of 12 Corbis

9. Kendall & Julian Brooks

Julian Brooks was Kendall Jenner's high school sweetheart. Oh, the pains of young love!

10 of 12 Splash

10. Kylie & Shamari Berkley

Jenner received a traffic ticket in Los Angeles while Berkley was a passenger in her car, and the two famously snuggled in a photo on the hood of Jenner's Mercedes. She even has a pet name for him: "Shamroo."

11 of 12 Splash

11. Kendall & Jaden Smith

Reportedly, Smith mentioned that he was "in love" with Kendall.

12 of 12 Corbis

12. Kendall & Corde Broadus

Following the Nickelodeon Kids' Choice Awards a few years back, it was rumored Kendall was texting up a storm with Snoop Dogg's son, Corde Broadus. Signs point to no on this one, though