Holly Willoughby mortified as her first boyfriend reveals ‘naked woman’ note she sent

Former This Morning presenter Holly Willoughby’s past came back to haunt her when she was reunited with her first love in front of a live audience and he brought with him a personal letter she wrote

Holly Willoughby has been reunited with her first love as part of Michael McIntyre’s Big Show, and the sweet moment was not without embarrassment for the former This Morning star.

Holly went red as Michael brought her childhood boyfriend Oliver onto the stage and interviewed him in front of the star. She giggled as Michael asked whether Oliver had any memorabilia or keepsakes from their romance, and she squealed “Oh God!” before Oliver replied: “It’s funny you should ask that,” and produced a letter from his pocket.

“Oh my god, what is that?” asked Holly, and Oliver said: “This is pure coincidence but my mother has had this and she sent it to me about six months ago. It’s a letter from you, Holly, to me.” Michael then asked Holly to read the letter aloud to the live audience in the episode to be broadcast on Saturday 22 February.

Holly on The Big Show
Holly cringed when the love letter appeared on screen 
Image:
BBC/Michael McIntyre’s Big Show S8 – 22-02-2025)
“Dear Oliver, how are you. have good time on holiday and get brown (if you can). I love you hope you love me and what about the photo of the naked lady Hannah was telling me about. Love Holly.” There was also what looked like a lipstick kiss at the bottom of the page.

Reading it out, Holly cringed and said, “this is so embarrassing,” then held her head in her hands. “It looks like I wiped my mouth with it,” she added, referring to the kiss at the end.

It’s not the first time Holly has fallen victim to Michael McIntyre’s sense of humour. In the fourth series of Big Show in 2018, she handed him her phone as part of the ‘Send to All’ segment and he sent an embarrassing text to all her contacts.

The message read: “As you know, I am a global style icon. This Morning are doing a feature where I help people with absolutely no dress sense and I immediately thought of you. What WAS that hideous thing you were wearing last time I saw you? Hope you won’t be offended but could you come in with a few of your outfits for Phil and I to laugh at. In return you’ll get a whole new wardrobe. What do you say? Need to know ASAP. Love Holly xxx”

Oliver on The Big Show
Oliver was Holly’s first love 
Image:
BBC/Michael McIntyre’s Big Show S8 – 22-02-2025)
Among the people who responded were her children’s head teacher, who wrote back: “Yes of course, but I’ll probably be busy with pre-prep assembly. Are my suits really that bad?”

Holly left her presenting job at This Morning in October 2023, following more than 14 years in the role. She recently returned to our TV screens for the new series of Dancing on Ice, and also for the Netflix show Celebrity Bear Hunt, alongside Bear Grylls.

The 44 year old hosts the show in which 12 celebrities try to escape the survival expert who is pursuing them through the Costa Rican jungle. After filming the show, she said: “There were a few moments on this show where I had to dig deep and have a strong word with myself. At those times, it was good to have someone like Bear next to you saying that being brave is about using that fear, harnessing it and doing it anyway.”

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