First dates can be awkward, amazing, or disastrous - even for famous people. Celebrities willing to share their stories prove that winning an Oscar or starring in a blockbuster doesn't matter; romantic chemistry does. From marriages to disasters, these celebrity dating stories share the good, bad, and embarrassing. Vote up the first-date memories that made you laugh or cry the most.
About this list
- 1

Denzel Washington met his future wife, Pauletta Pearson.They met on the set of the 1975 television biopic.The 1975 television biopic.Wilma.The two-time Academy Award winner took Pauletta on their first date in 1977. Washington was still an actor struggling but took Pauletta to a nice dinner.
The issue arose because Washington lacked enough money for the cab ride. Denzel told the story of their first date onJimmy Kimmel LiveShe paid.A 2017 interviewDavid Harbour started acting in the early 2000s. His role as police officer Jim Hopper in Stranger Things made him a household name. He also played a Russian soldier in the 2021 MCU film Black Widow.
Harbour ate his way up to 280 pounds for the part, filmed in 2019—the same time he met his future wife, singer Lily Allen.
She paid.
The couple married in 1983.
34 - 2

David Harbour started acting in the early 2000s. His role as police officer Jim Hopper made him a household name. He also played an imprisoned Russian soldier in the 2021 MCU filmTennon and Davis went on a date. They hit it off, and Tennon acted like a gentleman at the end of the night. Davis recalled:ate his way up to 280 poundsTennon called Davis twice after their date, twenty minutes apart. Davis said regarding Tennon's second call, "I just want to tell you I got home, and you are a beautiful woman. I’m about to go to sleep, and I just wanted to tell you to have a good night."The couple married in 2003.for the part, which he filmed in 2019—the same year he met his future wife, singer Lily Allen.Harbour described meeting her at his heaviest:
His wife met him at 280 pounds with this beard and this hair. They went on a date at the Wolseley restaurant in London, and she fell for him at his worst, physically and in terms of hair. As things moved forward, he began losing weight and working out. She has mixed feelings about this, which is a good place to be in a relationship. Starting the relationship from this point, instead of being the young, handsome guy and watching yourself decline over years, is really good.
The couple married in 2020.
.Once upon a time, Viola Davis was just a struggling Hollywood actresstrying to find a decent man
25 - 3

in Los Angeles. Davis complained about her dating problems to a friend when Julius Tennon overheard their talk.Tennon and Davis went on a date. They clicked, and Tennon acted like a gentleman at the end of the night. Davis recalled:He said, “You are a very beautiful and nice woman, and it was a pleasure spending time with you.” He shook my hand.
Tennon called Davis twice after their date, twenty minutes apart. Davis said about Tennon's second call, "I just want to tell you I got home, and you are a beautiful woman. I’m about to go to sleep, and I just wanted to tell you to have a good night."
The couple married in 2003.
Kelly Clarkson shared a bad first date story during a 2016 appearance on
The Ellen DeGeneres Show
24 - 4

. TheAmerican Idol winner and talk show host said that when she was an 18-year-old waitress, she reluctantly went out with a customer who would not accept "no" for an answer.Her date was an inch shorter than her and stood at 5'2". Clarkson had no issue with his height, but he clearly did. Clarkson admitted she is self-deprecating, but thinks there needs to be a clear line: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 spoke for a full hour about his height. I stood there for an hour too, then I went to the bathroom and left.
Clarkson felt bad for ghosting her date. “I’m going straight to hell,” she said. “It’s the worst thing I’ve ever done.”
20 - 5

Barbra Streisand and Josh Brolin met.They set up on a blind date.Streisand admitted she did not immediately swoon for her future husband, even though he “knew right away.”
A 2021 interview on The Tonight Show featured them.The Tonight Show.The legendary actress/singer/director kidded Brolin about his hair on their first date:
I expected a guy with a brown beard and wavy brown hair, like a mountain man. I saw a guy with all his hair cut off, no beard. I walked by him. I put my hand through his hair and said, “Who f*cked up your hair?”
The couple married in 1998.
19 - 6

George Clooney seemed set to stay Hollywood's most eligible bachelor. Then,Clooney met Amal Alamuddin.in 2013 through a mutual friend, and the pair instantly clicked.
Clooney worked on the score for his 2014 film in London.The Monuments Men.Amal lived in London then. The suave actor saw a chance to impress the human rights lawyer on theirThis was their first date.Clooney said during anClooney gave an interview with Howard Stern.:
We were scoring at Abbey Road. I thought, “If you're ever going to impress anybody, it's with a 150-piece orchestra at Abbey Road.”
The Academy Award winner took Amal to dinner in London that night. Clooney said, “We were together from that moment on.” They married in 2014.
17 - 7

Daniel Radcliffe became the face of the Harry Potter series.Harry Potter.franchise when he was only 11. The main role instantly made him famous worldwide.
The.The British actor said something.he always tried to keep his dating life out of the spotlight:
I just went out with a cap on. You have to hope the person you date is understanding and not made awkward by someone showing up. But you just do it. That was always the odd thing.
Despite his fame and money, Radcliffe said he had a normal childhood:
People always imagined I lacked a childhood or missed out on things. I know I had a very different childhood, but I still had those first dates and first kisses, those rites of passage. They were private. I did not feel like sharing them with the world; they were mine, which is good.
17 - 8

Timothée Chalamet is more than just a.He is a bestie to Kiernan Shipka.. The actor also acts as her safety net.
The.Mad Men.andChilling Adventures of Sabrina.star revealed during an interview with Seth Meyers that she asked Chalamet to join her after a guy asked her to lunch:
I did not know the vibe yet, so I brought a friend. Timmy was the only person there, so I brought him. Sometimes, when I wanted to hang out with a guy and unsure about a relationship, I would bring a friend; he was usually the friend I brought, like a big brother.
15 - 9

Singer Meghan Trainor andSpy KidsActor Daryl Sabara had an all-American type offirst dateThey went bowling and sang karaoke.
Sabara made his move at the bowling alley, and Trainor instantly liked his kissing skills:
He kissed me at the bowling alley. I told my security to step outside because I did not want to be watched. LOL. He was the best kisser ever. I know I am good at kissing, but I was shocked when he was.
The couple married in 2018.
12 - 10

Aaron Paul calls himself a "hopeless romantic"
In 2013, theBreaking BadActor revealed he met his wife Lauren Parsekian at the Coachella music festival in California. Paul said they came close to sealing their first date deal:
Our first date after Coachella was a trip to Vegas. We bought our first child a baby leather jacket from All Saints. We also jumped into a cab and said, “Take us to the nearest chapel. We're getting married.” The Little White Chapel was closed. We probably would have gone through with it. It would have been a funny story. But I am happywe got marrieda year later.
9 - 11

What is more romantic than dinner… and laundry? Comedian Tiffany Hadish talked about her worst date during achat with TMZ:
I went on a date with a guy to wash his clothes. He said we were going to dinner, and we got dinner, and then we went to the laundry house and washed [his] clothes. I am not a maid.
5 - 12

During a2021 interview, Jimmy Kimmel asked Charlize Theron about herworst date ever. The Academy Award-winning actress said she went out with a “super handsome” guy in her 20s. After a dinner date, he drove her home. Theron let him know she wanted a goodnight kiss:
He pulled over by my house, we started kissing, and it was really good. Then he pulled away and whispered, “Make out with my nose.” He was really into it, and I started giggling. It was good, so I did not want to miss it, so I gave him a little peck on the nose, and he said, “No, make out with it.”
3
More like this

Actors On Their First Year In Hollywood
Over 400 fans voted on 10+ actors who shared their struggles in Hollywood's first year. The top 3: Chris Pratt, who ate scraps off customers' plates as a waiter when he couldn't afford food, and Ryan Reynolds, whose Jeep was stripped.

Best Hot Ones Guests
Over 7,000 fans voted on 160+ guests for Best Hot Ones Guests Ever, with Paul Rudd, Gordon Ramsay, and Conan O'Brien currently in the top 3.

Greatest Entertainers Of All Time
Meet the greatest entertainers of all time, ranked by fans, from Michael Jackson to Freddie Mercury. Vote for legendary performers who shaped entertainment history.

The Best Male Actors Working Today
Over 148K fans voted on 290+ people in Best (Male) Actors Working Today, with Morgan Freeman, Leonardo DiCaprio, and Denzel Washington currently in the top 3.

Comments (0)
Join the conversation
Sign in to share your take and reply to others.
First take? Share what stood out to you.