Famous People Share Stories About Their First Dates

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Vote up the first-date memories you cherish.

First dates can be awkward, amazing, or downright disastrous - even for famous people, according to celebrities willing to share their dating stories. Some celebrity first dates went so well they eventually led to marriage. Others… not so much.

On a date, whether you've won an Oscar or starred in a blockbuster franchise really doesn't matter; it's the romantic chemistry that counts. 

It’s the good, the bad, and the embarrassing of celebrity dating stories. Vote up the first-date memories that made you laugh (or cry) the most.


  • Kelly Clarkson spilled a disastrous first date story during a 2016 appearance on The Ellen DeGeneres Show. The American Idol winner and talk show host said when she was an 18-year-old waitress, she reluctantly went out with a customer who wouldn't take “no” for an answer.

    Her date was an inch shorter than her and stood at 5'2''. Clarkson didn't have a problem with his height, but he clearly did. Clarkson admitted she is a self-deprecating person, but thinks there needs to be a fine line: 

    He proceeded to talk about his height for, like, a solid hour. And I withstood an hour, and then I went to the bathroom and I left.

    Clarkson felt bad about ghosting her date. “I'm going straight to hell,” she said. “It's the worst thing I've ever done.”

  • Kiernan Shipka Brought Friend Timothée Chalamet On First Dates For Security
    Photo: Chilling Adventures of Sabrina / Netflix

    Timothée Chalamet is more than just a bestie to Kiernan Shipka. The actor also seems to serve as her safety blanket 

    The Mad Men and Chilling Adventures of Sabrina star revealed during an interview with Seth Meyers that she asked Chalamet to come with her after a guy asked her to lunch:

    I didn't necessarily know what the vibe was yet, so I wanted to bring a friend. Timmy was the only person around so I brought him. One or two times when I wanted to hang with a guy and I didn't really know if I wanted it to be a thing or not, I would bring a friend and he was usually the friend I would bring… like a big bro.

  • Barbra Streisand and Josh Brolin were set up on a blind date. Streisand admitted she didn't immediately swoon for her future husband, even though he “knew right away.”

    During a 2021 interview on The Tonight Show, the legendary actress/singer/director said she kidded Brolin about his hair on their first date:

    I expected a guy with a brown beard and brown, wavy hair, like a mountain man. And I saw a guy that had all his hair cut off, no beard. And I walked by him. I put my hand through his hair and said, “Who f*cked up your hair?”

    The couple married in 1998. 

  • Denzel Washington's Wife, Pauletta, Paid On Their First Date Because He Didn’t Have Enough Money
    Photo: Tinseltown / Shutterstock.com

    Denzel Washington and his future wife Pauletta Pearson met on the set of the 1975 television biopic Wilma. The two-time Academy Award-winning actor took Pauletta out on their first date in 1977. Washington was still a struggling actor at the time but managed to take Pauletta to a nice dinner.  

    The problem came when Washington didn't have enough cash left over for the cab ride. Denzel told the story of their first date on Jimmy Kimmel Live during a 2017 interview

    I was gonna splurge and we were gonna take a cab, and the meter’s going, and I’m going, “Uh-oh… how far away does she live?”

    She paid. 

    The couple married in 1983. 

  • George Clooney Took Amal Clooney To Abbey Studios In London For A Movie-Score Recording To Impress Her
    Photo: magicinfoto / Shutterstock.com

    George Clooney seemed destined to remain Hollywood's most eligible bachelor. Then, Clooney met Amal Alamuddin in 2013 through a mutual friend, and the pair instantly hit it off. 

    Clooney was in London working on the score for his 2014 film The Monuments Men. Amal was living in London at the time. The suave actor saw an opportunity to impress the human rights lawyer on their first date, Clooney said during an interview with Howard Stern:

    We were scoring at Abbey Road. And I thought, “If you're ever going to impress anybody, it's with a 150-piece orchestra at Abbey Road.”

    The Academy Award winner also took Amal out to dinner in London that night. “We were together from that moment on,” Clooney said. They married in 2014.

  • Daniel Radcliffe became the face of the Harry Potter franchise when he was just 11 years old. The titular role instantly catapulted him into international fame. 

    The British actor said he always attempted to take his fame out of the picture when it came to his dating life:

    I just went out with a cap on, and you have to hope that the person you’re dating is understanding and not made to feel awkward by someone coming up or anything like that, but you just do it. That was always the weird thing.

    Despite his fame and fortune, Radcliffe said he experienced a normal childhood: 

    I think people always imagined that I didn’t have a childhood or I missed out on some stuff, and I’m sure I had a very different childhood, but all those first dates and first kisses, those rites of passage, I still had them, and they were actually generally really private. I don’t feel like I have to share them with the world, and I felt like they were really my own, which is nice.