14 Times Celebs Allegedly Dated The Ex Of Family Member Or Close Friend

From 2014–2015, dating rumors swirled around Kendall and Justin.

In 2014, she told Nightline, “He’s a longtime friend of our family. Everybody loves to assume things, but no.” 

However, Justin seemingly suggested they’d casually dated, telling Billboard it was “never serious” between them.

Then, in 2016, he and Hailey dated for a short time, but their relationship ended in a “very dramatic excommunication.” However, two years later, they reunited at a Miami church conference and got engaged a month later.

Hailey told Vogue, “The common denominator, I promise you, is always church. By then we were past the drama. I just gave him a hug. By the end of the conference, he was like, ‘We’re not going to be friends.’ I was like, ‘We’re not?’”

In a 2020 Instagram Live with the trio, Justin asked Kendall, “Quick question, did you see this coming?”

She replied, “See what coming? You two? … Erm, honestly… No. I didn’t know but I think I hoped. Obviously Hales is my lady and my best friend and I, like, wanted it so bad for both of you.”