Tuesday, September 15, 2026

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Jessica Simpson: Ryan Gosling and Justin Timberlake bet who could kiss me first

Jessica Simpson claims Justin Timberlake won a bet with Ryan Gosling to kiss her first.
The 39-year-old singer has revealed she shared a cosy moment with the ‘Can’t Stop The Feeling’ hitmaker – who she first met whilst auditioning for ‘The Mickey Mouse Club’ with Ryan – after her divorce from Nick Lachey.
Spilling to Jimmy Kimmel on his show on Wednesday (29.01.20), Jessica recalled: "He was over at my house and we shared a nostalgic kiss."
Things suddenly took a turn as Justin, 38, began texting someone straight after their encounter, before explaining his teenage bet with the 39-year-old actor.
She continued: "He took his phone out and started typing. I was like, ‘Okay, I hope that’s not like another girl. Did I stick my tongue out too much?’
"Apparently him and Ryan Gosling had a bet on who would kiss me first when they were 12-years-old, and so he texted Ryan and told him he won the bet. And I was like, ‘Oh, okay? So we don’t kiss again?’"
However, it was the ‘Notebook’ star that Jessica originally had her eyes on.
She explained: "Ryan was the one that when I was 12, I was like, ‘This guy is so cool. He’s from Canada; I don’t know where that is on the map, but I really think that that’s amazing and there’s something so cute about him.’ "
The news of the childhood bet comes days after Jessica confessed she became hooked on diet pills after she was allegedly told to lose weight by her record boss when she was a teenager.
She claimed she was urged by record label chairman and CEO Tommy Mottola to lose 15 pounds at the age of just 17 in order to be signed and make it as a pop star.
Writing in her new memoir ‘Open Book’ – which is set for release on February 4 – Jessica said that "he wanted to sign me" but he allegedly said: "You gotta lose 15 pounds."
When Jessica questioned his remark, he reportedly replied: "That’s what it takes to be Jessica Simpson."
Straight after the meeting, Jessica – who was 5ft3 and weighed 118lbs at the time – went on a "strict diet".
She explained: "I immediately went on a strict diet.
"And I started taking diet pills, which I would do for the next 20 years."

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