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Celebs’ most embarrassing romantic love affairs revealed

Posted on February 11, 2023

They may live in multi-million dollar mansions, travel the world, and pay out huge paychecks, but when it comes to romance, celebrities are just like us.

From awkward first times to awful kisses and terrifying dates, A-listers have had their fair share of love-life disasters.

Channing Tatum seduces Sombero

Jenna Dewan has revealed how her ex-husband Channing Tatum seduced her while filming her hit film Step Up and confessed he had an unusual choice of outfit.

“He’d dated all the dancers on ‘Step Up’ and had this crazy wild tequila night,” the actress recalled.

Determined: Jenna Dewan has revealed how her ex-husband Channing Tatum seduced her while filming her hit movie Step Up (pictured in his hit movie Magic Mike)

“He said he had a chance to ‘be free’ and he couldn’t stop thinking about me. So he comes into my hotel room at two in the morning and knocks on the door. I’m like, ‘What’s up?’

“He’s wearing a sombrero, underwear, ugg boots and he’s like, ‘Let’s do this.’

Ed Sheeran’s 007 hickey

First kisses aren’t like the movies, as Ed Sheeran found out as a teenager.

“My first French kiss was probably like everybody’s first French kiss,” the singer said, pointing out that the teen dramas of the noughties helped a lot of people his age orient themselves.

“I think if you’ve watched a lot of One Tree Hill or The OC your first French kiss would probably be spot on because you’ve studied it, but I hadn’t watched any of those programs.”

Instead Ed. famous for his love songs, was inspired by the ultimate ladies man – 007.

“I think the first kiss I saw on TV was in a James Bond movie where Pierce Brosnan just put his tongue in, so yeah it was one of them! Very uncomfortable and wet.

Inspired by Bond: First kisses aren’t like in the movies, as Ed Sheeran found out as a teenager

Miley Cyrus’ first night with Liam

Miley Cyrus’ marriage to Liam Hemsworth may have failed and burned, but the star has recalled that the Australian hunk was her first love.

“I didn’t go all the way with a guy until I was 16 … but I ended up marrying the guy,” she said on Barstool Sports’ podcast “Call Her Daddy.”

“I lied and said he wasn’t the first so I didn’t seem like a loser,” she added of her first night with Liam, whom she married in 2018.

Ex: Miley Cyrus’ marriage to Liam Hemsworth may have failed and burned down, but the star has recalled that the Australian hunk was her first love

Michael Douglas’ VERY bold chat-up line

After seeing her on screen and falling in love with her, Michael Douglas was determined to land a date with his now-wife, Catherine Zeta-Jones.

At the Mask Of Zoro premiere in 1998, he styled an introduction from pal Danny Devito, and after landing a drink date, he had his best chat-up line ready – telling her, “I’m going to father your kids be.”

Catherine wasn’t impressed, telling the legendary actor, “I’ve heard a lot about you. It’s nice to know it’s all true. Good night,” he stormed out of the bar.

However, there was a happy ending when Michael managed to win over the actress and now they have a 22-year marriage and two children between them.

Love at first sight: After seeing her on screen and falling in love with her, Michael Douglas was determined to land a date with his now-wife, Catherine Zeta-Jones

Zayn Malik’s size dilemma

He’s got a Victoria’s Secret model as his ex and millions of swooned fans worldwide, and even as a 13-year-old, Zayn had some traits trying anything to overcome a first kissing hurdle.

“I was very short and she was very tall, so I had to put a brick against the wall and stand on it to reach her face,” he told Seventeen magazine.

Confidence: Even as a 13-year-old, Zayn had some traits trying anything to overcome a first kissing hurdle

Jennifer Aniston’s first date misunderstanding

Jennifer revealed how she once took a group of friends out on a date with former The Daily Show host Jon Stewart.

Jon, who appeared on the show in 2010, reminded Jennifer of the awkward moment.

“I asked you out and it was lovely. I remember you brought so many of your friends with you. And I remember thinking, “She’s so excited to go on a date with me, she wants me to meet her crew,” Jon said.

But Jennifer recalled things differently, insisting, “If I remember correctly, it wasn’t something like, ‘Hey, a group of us are going out, want to join us?’

Awkward: Jennifer revealed how she once took a group of friends out on a date with former The Daily Show host Jon Stewart

Joe Jonas’ desperate search for protection

The Jonas Brothers star spoke to fans about his first time during a very candid Reddie AMA.

“I lost my virginity to this girl named Ashley. You can probably just google it. It’s pretty easy to find out. I’ve dated a girl named Ashley, so just google it to find out which Ashley that is,” he began.

However, things didn’t quite go to plan “because I didn’t have condoms,” he revealed.

“So I went into the room of our drummer Jack, who was my roommate at the time, and destroyed his room looking for them. Found them under his underwear drawer.”

“When he got home he thought someone broke into his room because his whole room had been demolished because I needed it badly. Had to happen then and now. Safety first, kids.’

Reveal everyone: Joe Jonas spoke to fans about his first time during a very candid Reddie AMA

Salma Hayek’s date dupe

Salma Hayek and her CEO husband Francois-Henri Pinault’s first date wasn’t even a date, according to the actress.

“I didn’t know it was a date. I thought I was going to an event and there was one person there,” she recalls.

“I was fooled by friends into going to an event because they knew I wasn’t going on a date! I was mad. And he didn’t know because he thought I knew he was just coming to meet him.”

Going blind: Salma Hayek and her CEO husband Francois-Henri Pinault’s first date wasn’t even a date… according to the actress

Demi Lovato’s extreme second date

While most second dates involve dinner and drinks, Demi got more than she bargained for with one of her exes.

“I had an appointment with someone and they invited me to this trip [to Hawaii]so I was super excited,” she recalled.

“And they said, ‘We have a surprise today,’ and I said, ‘Okay? What do I wear?” and they say, “Dress comfortably.” So I put on this silk jumpsuit with wedges, ready to go, and I walk out of the room, and they say, “This isn’t going to work,” she said Ellen DeGenerous on her show.

Demi soon found out she wanted to go skydiving for their second date. “We walk and we jump from the highest point you can reach without an oxygen tank, which is 14,000 feet (almost 44.3 km) or higher. We fell free for two minutes and I couldn’t say no!’ she insisted.

Not What She Expected: While most second dates involve dinner and drinks, Demi got more than she bargained for with one of her exes

Rihanna’s traumatizing first kiss

In an interview with Rolling Stone magazine, Rihanna admitted that their first kiss was “the worst thing that ever happened.”

“He pretty much poured his entire salivary glands into my mouth. It traumatized me. I haven’t kissed, like, ever,’ she said.

‘It traumatized me’: In an interview with Rolling Stone magazine, Rihanna admitted that their first kiss was ‘the worst thing that ever happened’

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