Harry Styles Hops Into Bed With Cougar Chelsea Handler

The two have been close pals for a while, but their relationship began to raise eyebrows in 2015 at a house party in LA, where they were reportedly inseparable. The pair allegedly would not leave each other's side, and escalated their flirtation when they wound up in bed together at the party! "They seemed to think nothing of the commotion they caused by plonking themselves together side by side in such an intimate setting," a source told The Sun. "They were on a bed as people rushed around them and they were being pretty flirty."

Handler, 41, has had no qualms about sharing her love for younger men, and 22-year-old Styles has a track record of dating women much older than himself. He dated 32-year-old TV presenter Caroline Flack when he was just 17, before moving on to Nicole Scherzinger, who is 15 years his senior.

As RadarOnline.com reported, Styles took a short break from dating older women in order to share a romance with Jenner, but that allegedly ended after he was caught cheating on her with a stylist in London.

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"Being wild is Chelsea's natural default behavior and Harry is a free spirit who doesn't care how his actions look to others," an insider said. "But it certainly was the talk of the bash."

Accordingly, friends say that they are keeping their relationship playful. "Harry and Chelsea are friends through Jeff and love to mess around," a source shared. "Any suggestion they have taken things any further than friendship is incorrect."