Ever Wondered What It Would Be Like to Date a Celeb? Just Ask These People

Remember the icebreaker game “name your celebrity crush?” A large number of us were actively involved in this game, hoping we would get a chance with our dream celebrity crush, and we haven’t given up on that.

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For some, it became a reality, getting to go out with Grammy Award-winning singers, Academy Award nominees, and even future presidents. Here’s a breakdown of regular people who dated celebs and what they were really like.

The Food Blogger and the Musician

Guess who? The most crushed on celebrity got himself hooked up with a food blogger in May 2017 after they were introduced through a mutual friend. His fans went crazy when she was spotted with his shirt.

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But by June of that same year, it was rumored they broke up, and their short-lived romance gave her the suitable attention for her blog.

I Wish It Never Happened

Not our Brad Pitt! There is no doubt about him being multi-talented after being a part of the golf, tennis, and swimming teams and part of the musical and debates team while in high school.

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He seems perfect at everything, but he was proved wrong when he burped on his friend’s face while kissing her. Now that’s an image you can never unsee in your mind.

A Downstairs Romance Featuring Taylor Swift

This scenario is like one from a movie, and it features Taylor Swift, her high school, Wyomissing Area Senior High School, and her ex-boyfriend. They made out in the basement, but people would say, “he kissed her downstairs.”

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We wonder what happened to him and if he still tells the story about the “downstairs” kiss with Taylor.

She Lost Gem

She didn’t think our never-aging George Clooney was going to become the world’s treasure he became after a dinner date she had with him in the 90s.

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To her surprise, he received two Primetime Emmy Nominations in the same year, but he broke into world domination by the 2000s, especially in 2001. However, Goerge got married to a regular person like us, maybe more successful than us.

Miscommunications, Hook-Ups, and In Her Fifties?

A blind date filled with several miscommunications. This aunty had a blind date with Gerard Butler, but there was confusion instead of a smooth date. The movie star had planned for a hook-up and not a supposed blind date.

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The aunt was a French-Canadian woman in her fifties hoping for romance. She was decades older than him, and they had a sweet lunch and laughed about the unfortunate mistake.

He Couldn’t Handle a Hot Flirty Woman

Before Charlize Theron became famous, she met this young man who was an extra for a movie she had auditioned for. It was a small role, and she hadn’t been made yet. He got shy and backed away, and soon after, she rose to fame.

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He must have been punching the air, watching her attain stardom, and regretting his move to back away, but what’s meant to be will be.

Too Focused but on a Different Thing

Keanu Reeves attended four different high schools, and in one of them, he dated this friend’s mom. Keanu wasn’t a child actor, neither was he a part of the school drama club; instead, he was into music and was in a band he created with his friends.

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He got dumped by her because he spent more time with his music friends than with her, and by the time he was 15, he decided to take acting more seriously.

Weird and Unexpected Funny Al Yankovic

His aunt dated the Weird Al Yankovic, the comedian who knew his craft, sold more than 12 million albums and counting and had his first comedy song aired in 1976. He even has five Grammy Awards to his name.

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While Alfred Mathew Yankovic dated this guy’s aunt, he met with their family, and to their surprise, he was even funnier than they expected him to be. I believe his career choice was loud enough to say “I am funny,” but I guess they underrated him.

A Third Grade Romance Gone Sour

This short-lived child romance didn’t last, but it hurt our storyteller. He went to the same school with our very own Isla Fisher at the Swanbourne Primary School, and in third grade, they held hands. That does sound cute.

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After the school holidays, she returned to school, but her interest in him had already vanished. It is understandable because children that age lose interest in everything.

Drunk at My Ex’s Wedding

This wasn’t a smooth one for Matthew McConaughey, and it wasn’t one of his good moments. He dated the aunt of this person and even got invited to her wedding. He went but got so drunk he refused to leave and passed out in the back of their family car.

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Her father wasn’t pleased with his behavior and has refused to watch any of his movies since then. Mathew’s terrible night made him lose a fan, but that didn’t stop him from taking Hollywood by storm; we just hope he isn’t getting drunk at weddings.

A Simple Life

Tell me you made out with Paris Hilton without telling me you made out with Paris Hilton; ask my friends. This guy shared this information with everyone willing to hear.

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Paris Hilton’s fame had just begun to rise with the reality show “A Simple Life” when she met this mister at a club where they made out in the bathroom. Although he complimented her kissing abilities, he is still a tattletale for being a kiss and tell.

Why My First Instagram Post Is Leonardo DiCaprio

This wasn’t a date, but a hangout between college students, and Leonardo DiCaprio decided to join; he was curious about their lives as college students and wanted to know what it was like. They were ecstatic and enjoyed his company.

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One of the students made the hangout with him her first Instagram post. She also mentioned how he let her try out his udon. I see absolutely nothing wrong in making Leonardo your first post. I see nothing wrong with what he does.

Daniel Radcliffe Gave the Best Birthday Surprise

We don’t mind if this is crowned as one of the sweetest gestures made by an actor. Daniel Radcliffe didn’t just make his girlfriend at the time and her family comfortable; he extended his hands of sweetness to her family friend too.

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He sent him a personal birthday text without knowing this fellow because his girlfriend told him about it. That seemed pretty cool, and since many of us watched him grow into that man he is now, it still feels great to see him doing good.

I Got Sloppy Kissed by Renee Zellweger

This waiter got a sloppy drunken kiss from actress Renee Zellweger while they were in town shooting scenes for “Leatherheads.” He clearly didn’t mind and hoped they could have met up after his shift, but she immediately left in a cab.

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He mentioned she called him cute and told her friends how cute he was. He was leaving the kitchen when she met him halfway as she left the female’ bathroom and planted the sloppy kiss right on his mouth (but shouldn’t that be sexual assault?).

A Little Too Slow for a Runner

How do you catch a jog with Harrison Ford, have him talk about the movie he would star in, and not realize who he was until he left? That’s one unlucky jogger, and that’s the friend of the sister-in-law we have next.

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According to her, Harrison Ford jogged with her and talked about the shooting of “Star Wars: The Force Awakens.” It might have looked like she missed an opportunity, but it sounded like she had a lovely jog with him.

It Was So Bad She Didn’t Like to Talk About It

Getting to date Justin Bieber is a lot of girls’ dreams, and before he was off the market, he had dated several people, including this godmother’s daughter. But for her, it wasn’t a delightful experience, and we wonder why.

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She never liked to talk about it when asked about it and would avoid the conversation or simply ignore questions about the unfortunate relationship. As for Justin, we never heard of this relationship from him, and he has since been married to a supermodel, Hailey Baldwin.

What Happens in Mexico Stays in Mexico?

The witty and brilliant American comedian, actor, writer, and producer Rainn Wilson is known for several productions and acting skills. He has three awards for the Outstanding Supporting Actor in a Comedy Series to show for it.

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Yet there was this report of a school teacher concerning him. He said that they dated for three months and went to Mexico together. But she would never talk about what happened there because what happens in Mexico stays in Mexico.

Not Another Lonely Night

The loneliness of Samantha Fox during her 80’s tour is a sad tale to remember. It was so bad she told one of her security guards to keep her company because she hated eating alone and she didn’t want to go out. It was charming and thoughtful that he agreed.

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While they had a quiet dinner, her experience with her security guard is proof that fame and crowds don’t equate to intimacy, and whether famous or not, we all want company in our lives.

Nice But Not Good Enough

Back in the 1970s, Bill Murray was just building his name, and the excitement he felt could not have been avoided. Well, our next regular person agreed, but she thought he was so full of himself.

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She admitted that he was a good person and must have been excited about his growth; he just wasn’t good enough for her and ended the relationship. He was pretty young, by the way, and had just moved to NYC for more significant roles.

The Perfect (Justin Timberlake) Gentleman

Just before Justin Timberlake met Jessica Biel, he dated this young man’s mom and proved himself to be the heartthrob the world knows him as. Justin went all out expressing his romantic side with her.

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He would hold doors for her, get her flowers, and be the amazing gentleman he was. This set up a standard her ex-husband couldn’t keep. On the other hand, Justin and Jessica are still happily married with kids of their own.

Chuck Norris Wasn’t Good Enough for Nana

This Nana must have been the life of the party if the legendary Chuck Norris was such a bore. A date was arranged between Nana and Chuck, and while her sisters and cousin waited for her to tell them the details, they weren’t prepared for this disappointment.

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Facts about Chuck Norris began to spread and to realize he was a top gun celebrity, their interest in their date grew, and when they finally asked about him, she said, “he was a lovely man, but honestly a bit of a bore.” The second date never happened.

From Eating Chili Dogs to Glamour Queen

We could never have imagined Selena Gomez chowing down chili hot dogs trying to win a hot dog-eating competition with her then-boyfriend! This did happen while she was in high school, but the relationship ended, and they stayed friends.

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As she ventured into the entertainment industry as a young actor, school and high school relationships became a lesser priority. Her goal was to become world-famous, and she achieved that. We are all very proud of her growth.

Too Shy to Take a Compliment

Taika Waititi was Taika Cohen, a member of a folk parody duo called “Humourbeast” with Jermaine Clement before he became a well-known director, producer, screenwriter, actor, and comedian; before his redirecting work on “What We Do in the Shadows” and “Thor: Ragnarok.”

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While in the university, he dated several girls and was humble and easy-going, like he is to date. Back then, he didn’t enjoy his work being complimented because it made him feel uncomfortable. Apparently, he still feels this way.

Not My Type of Man

This is a good one. When you receive a love note, if you ever did, there might be a picture of a cupid, flower, or people kissing drawn on the letter. Either way, it is usually something cute. Well, Arnold Schwarzenegger thought himself to be the cute one, which is not wrong.

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But he drew himself on the love noted instead. Was he wrong? I mean, he won the Mr. Universe and Mr. Olympia multiple times. She didn’t find any of it cute and thought him too full of himself for her to date.

Fake a Memory Loss and She Might Believe It

Celebrities tend to meet different people and forget names but do they forget the names of people they dated? Her college roommate’s cousin, that’s right, had been going on several dates with Armie Hammer before “The Social Network” blew up, and he got famous.

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We’re not sure if he faked a memory loss or forgot that he used to go out with her, but they met after he got famous, and he tried to ask her out again, and she told him she knew him because they used to go out. All I have to say is that she must have been all that.

A Flopped Bubble Match

When you get a chance to know a celebrity, you miss out because you tried to make people become what you want them to be and not what they want to be. This unlucky fellow got a bumble match with child start Chloe Moretz.

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He told her he preferred her in darker roles, and she ghosted him. Chloe’s first hit role was in the supernatural horror movie “The Amityville Horror.” I guess she didn’t want to be reminded of the dark times of the past.

Johnny Depp’s Romance Involved Letters

Johnny Christopher Depp II, known as Johnny Depp, took the 90s by a heartfelt storm of romance, secrecy, and letters. A little birdie said that he would hook up with different aunties at their time, setting up romantic dinners with them.

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He loves to send letters too, but I wonder if any of those women still have his letter. Johnny Depp got ahead with his career and earned nominations for three Academy Awards for Best Actor and ten Golden Globes for the same category.

Before I Was Famous

I wonder how it feels when months after dating someone, they become insanely famous; this next person sure knows how that feels. She dated Mark Hamill when he was still a small-time actor, and they had gone out months before the “Star Wars” movie.

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After a particular date, she never heard from him, and then boom, she catches his different looks on Star Wars. What an unexpected twist. She did agree that he was friendly and humble, too.

All I Ever Wanted…

The following person didn’t expect Dax Shepard to choose acting as a career path. He attended Santa Monica and West Los Angeles College. He also graduated from UCLA with a B.A. in Anthropology, where he met his college sweetheart.

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They had met before he became famous, and she described him to be a “good-hearted man,” regardless of what he had studied, he chose a career path that involved putting a smile on the faces of many.

Experiencing the Unbelievable with Salma Hayek

The idea of your parent knowing her star before they became famous will always seem unbelievable except if there was a picture or video evidence, but how many people had phones while these stars were still young? Salma Hayek and the father were childhood friends who lived in “Heroica Veracruz,” a small town in Mexico.

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Our mister didn’t believe the story until Salma Hayek, his father, and himself ran into each other at the airport, and she invited them to her home for dinner. She was so welcoming and pleasant; it still felt unbelievable to this young fella. His father cleared his name and proved himself correct.

Name Dropping and Cheating

Norman Reedus might not have expected to attain the level of fame his role as Daryl Dixon in The Walking Dead got him, and we would expect humility from someone surprised about his growth, right? Wrong.

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Norman went from name-dropping celebrities he had met around his ex-girlfriend and her family to allegedly cheating on her with a co-actress he met set on the set of “Inglourious Basterds.”

A Song About His Exes

The hit song “Somebody That I Used to Know” is popular since we all have dedicated it to our exes but have you thought of the song’s origin? Our next person believes the song was written for his ex-girlfriend because it came out after she recently dated the Belgian-Australian singer-songwriter Gotye.

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But we can’t agree because the song seems to be referring to all past relationships. It was such a massive that it hit the top 10 on the music charts in more than 30 countries worldwide.

Too Proud to Handle

Not everyone wants to date a star, especially one who is so full of himself. This was confirmed when this person mentioned that his mom didn’t enjoy her date with Bryan Adams. She hated it so much that she didn’t agree to a second date.

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Her reason was that he was too full of himself. I can actually understand why since he built himself up from a $1 contract he signed in 1978 with his first label to make a name for himself; another incredible thing is that he wrote the hit “(Everything I Do) I Do It For You” in under an hour.

The Pink We Know Is the Pink She Has Always Been

We can attest that Pink went to Central Bucks in Pennsylvania, she joined a group called “Middle Ground,” and she wrote deep songs while in high school because her dear ex-boyfriend from high school shared those details.

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Her ex-boyfriend happened to be this fellow’s uncle, and in their words, their uncle was one wild teenager who did things like setting the neighbor’s pool on fire or creating napalm in his backyard. Even her mom agreed that her lyrics were “very introspective.”

I Wish I Wasn’t Intimidated

When you’re reminded about your wife’s ex buying a $150,000 watch because he was sad gets you sad, but that is not the shocking part; it’s the fact that she didn’t want that fame and stares from paparazzi or fans.

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This fellow’s wife dated superstar comedian Louis CK in 2021 but broke up with him because she didn’t like the fame. He even got an invite to her birthday after she married, which he attended; he remarked that he was relaxed and friendly.

Sweet on Set; Sweet in Reality

David Tennant is known for his roles on Broadchurch, Doctor Who, Harry Potter and the Goblet of Fire, Jessica Jones, and Hamlet. But what you don’t know is the regular people he has dated, although this didn’t lead to walking down the aisle.

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A college student mentioned that this Scottish actor dated her friend at college, and she said he was adorable. Now, I’m super curious, if he was lovely, why didn’t they walk down the aisle?

Sting Doesn’t Do Crazy

We get it: pain, heartbreak, terrible and toxic relationships bring out the best songwriters. Just ask Taylor Swift or Sting. He has an excellent story to tell. He dated (not my words) “a psycho,” and even her kid agrees. And he wrote songs about her.

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Her son shared the story, and he mentioned how he would sing “Roxanne” or “Message in a Bottle” to tease his father. But how bad would you want to tease your dad with a song that says, “he will never live up to the fame of his wife’s past suitor?” This shows that he is truly his mother’s son.

Grandma Once Said, “I Once dumped Elvis.”

Many of our grandmothers have claimed to have dated one star or the other, and a fan dating a star would be seen as problematic or a struggle for the fan because of the introduction into unprepared fame. Still, this grandma knew precisely what she wanted, and it wasn’t Elvis.

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Back then, there wasn’t social media and the intense drive to prove oneself by having a picture or video evidence, but her words here were as good as gold when she said, “I once dumped Elvis.” Her reason was that he had too many hungry women around him.

Amber Got the Last Laugh

This guy didn’t date Amber but met her during high school. He mentioned how she had her mindset on being a star and got laughed at for choosing that dream. He also says her humility was hanging out with the public school’s kids since she attended a private school.

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Well, she’s laughing now and in fame and wealth. This goes to say, proclaim your dreams, chase your dreams, never give in to hearsays, and never give up, just like Amber didn’t.

A Pickle on a Beach Kinda Date

Jimmy Buffet is a legendary singer-songwriter who loves to live his life as he wants and not as the people claim it to be or as his management suggests he does; this includes people he chooses to date.

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A must know about Jimmy is his gift of wooing women and how he could make eating a jar of pickles he got from a gas station at the beach romantic. We wonder if they had a second date, but whether it was an epic fail or not, this only proves Jimmy is as accurate as his music.