30+ Celebrities Who Said Goodbye to Stereotypes and Are Proud of Their Bodies

Celebrities / By TL LAM

Only a minimal range of body types was accepted in Hollywood for a long time. These days, though, Tinseltown has become a lot more diverse in its beauty standards. That’s not to say that there isn’t more work to do, but progress has definitely been made. However, these celebs have always been proud of their bodies — with or without the media’s approval.

Sam Smith

Sam Smith’s body image journey has been a very public one. The singer expressed, “In the past, if I have ever done a photoshoot with so much as a t-shirt on, I have starved myself for weeks in advance and then picked and prodded at every picture and then normally taken the picture down.”

Sam Smith

He continued, “Yesterday I decided to fight the […] back. Reclaim my body and stop trying to change this chest and these hips and these curves that my mum and dad made and love so unconditionally.”

Rihanna

Rihanna’s weight fluctuates quite a bit (whose doesn’t?) and now that she’s had a baby and is pregnant once again, it looks like we’re going to have baby bump Rihanna for a bit longer.

Rihanna

RiRi doesn’t seem like she’s going to argue that assessment anytime soon, as she’s said, “I know when I’m having a fat day and when I’ve lost weight. I accept all of the bodies. I’m not built like a Victoria’s Secret girl, and I still feel very beautiful and confident in my lingerie.”

Bella Thorne

Bella Thorne has past struggles with maintaining what she believes to be a healthy weight for herself. The actress said that she has a hard time eating when she’s stressed, which can lead to her feeling malnourished.

Bella Thorne

So as not to get worked up about gaining weight, Thorne has thrown her scale in the trash and encourages others to do the same. She exclaimed, “Throw away your scales, ladies […] As long as YOU feel better and you like the way you look that’s all that matters.”

Drew Barrymore

Drew Barrymore lost a whopping 20 pounds in 2020, and expressed that she was thrilled with the results! Barrymore got a personal trainer, dedicated herself to practicing yoga, and took daily workouts more seriously than she had in the past. The actress encouraged her fans by saying, “Just so you know, if I can do this, anyone can do it.”

Drew Barrymore

Well, anyone with thousands of dollars to shell out for a celebrity trainer. We get her point, though — and given that there are plenty of free workouts on YouTube, she’s right.

Demi Lovato

Demi Lovato has been very open with her fans about her struggles with body image. Perhaps she’s been a tad too forward with her feelings, for those who are familiar with the frozen yogurt shop debacle.

Demi Lovato

However, Lovato did get it right when she spoke about how she’s changed her perception of what it is to be beautiful. “All I have to say is, ‘I’m healthy.’ In that statement, I express gratitude. I am grateful for my strength and things I can do with my body.”

Hilary Duff

Hilary Duff suffered from an eating disorder when she was younger. So now, as an adult, she wants to shield her young fans from that fate. Duff has been extremely open about the fact that she exercises regularly, gets body makeup applied for photoshoots, and there’s always someone present whose job it is to make sure she looks good.

Hilary Duff

The actress has also clarified to her fans that while working on one’s body is important, Hilary wants to “work on the inside. That’s the most important part of the system.”

Rebel Wilson

Rebel Wilson famously lost 77 pounds over the course of two years. Wilson attended a wellness retreat, switched to a high-protein diet, lowered her daily calorie intake, made sure to stay hydrated, and took up walking.

Rebel Wilson

Some fans worried that Rebel had sold out to Hollywood’s beauty standards, but the actress quickly put those rumors to rest by saying, “For me, it was about being the healthiest version of me — it wasn’t about size or a number or whatever.”

Ashley Graham

Being a plus-sized model, Ashley Graham is no stranger to having her body scrutinized. Graham has spoken about her determination to do anything a model whose size zero would do. Ashley doesn’t believe in covering up in the summer, for fear of a belly roll or some cellulite showing.

Ashley Graham

On the contrary, she often posts photos of such instances on her social media. Alongside those pictures, Graham tells her fans, “Don’t let your mind stop you from enjoying your life to the fullest.”

Mariah Carey

Mariah Carey claims to embrace her body, but her tendency to edit her photos on social media tells a different story. We’re not judging — if we were constantly being scrutinized by the public, we’d probably do the same.

Mariah Carey

That being said, there’s some harm in creating unrealistic beauty standards. In her defense, Carey has admitted, “I have always had low self-esteem, and people do not recognize that.” If only body shamers didn’t make her feel compelled to alter her appearance…

America Ferrera

America Ferrera knows better than most how Hollywood can mess with someone’s self-esteem. The actress has said that she used to struggle with getting leading roles because she was seen as “too brown, too fat, too poor, too unsophisticated.” Nowadays, though, Ferrera is too far up the elite ladder to be denied serious work.

America Ferrera

She explains, “I grew up believing a lot of things about myself that I had to unlearn.” It seems like the entertainment industry had to unlearn some things, too.

Jonah Hill

Jonah Hill is proof that, sometimes, you need to make a change to improve your confidence — which is fine, as long as it’s for you and no one else. The actor lost over 40 pounds and has expressed that he’s happier in his new body type.

Jonah Hill

When asked about his secret, Hill explained, “I wish there was some crazy thing that I did, like a pill or a genie or something, but I went to see a nutritionist, and he told me what to eat to change my habits and stuff.”

Katy Perry

Katy Perry exploded onto the music scene just as hourglass figures started to come back in style, while thinner bodies were fading out. Perry’s well aware that she’s part of this cultural shift, as she’s said, “I’m curvy, I’m not sample size, but I represent a lot of people out there.”

Katy Perry

In recent years, Perry’s fitness routine has been moved to the back burner as she focuses on motherhood. Of course, that meant media scrutiny over her changed body, but Katy knows that she’s representing new moms everywhere.

Oprah Winfrey

Oprah Winfrey has often used her platform to discuss her struggles with body image and various diets over the years. These days, Winfrey has a strict exercise routine, even though she admits to hating it “so much.”

Oprah Winfrey

She has explained, “I think everyone’s waiting to love it. You’re not going to love it but you do the thing you need to do to make yourself feel whole and well.” For this celeb, it’s not about the number on the scale, but all about her health!

Melissa McCarthy

Poor Melissa McCarthy has had to deal with countless interviewers pretending to care about her health and well-being while calling her out for her weight on live TV. Truthfully, if they were really so concerned, they could’ve spoken to McCarthy about her size during the hours they were backstage in hair and makeup.

Melissa McCarthy

Of course, they always wait until there’s an audience. The actress isn’t buying into it, though, as she’s expressed, “My message is that as long as everybody’s healthy, enjoy and embrace whatever body type you have.”

Winnie Harlow

Winnie Harlow shot to fame as a contestant on America’s Next Top Model where she got her first dose of the judgemental industry when Yu Tsai insisted on calling her “panda” despite Harlow asking him not to.

Winnie Harlow

The rude nickname was a reference to the model’s vitiligo, an autoimmune disorder that causes patches of the skin to lose pigmentation. Resilient as ever, Winnie’s clarified, “I don’t find my beauty in the opinions of others. I’m beautiful because I know it.”

Selena Gomez

Due to her various health issues, Selena Gomez’s weight fluctuates often. However, in Hollywood, even a legitimate illness isn’t an excuse to pack on a few. Inexplicably, Gomez has needed to take to social media to explain her weight to critics.

Selena Gomez

The singer/actress let the public know that they don’t need to remind her of her changing body because she’s aware. She said, “Not a model, never will be. And I think they’re awesome, mind you, I just am definitely, definitely not that. So, that’s it.”

Lizzo

Lizzo has always been an advocate for body positivity, which is a big part of her personal brand. The singer has said, “Someone’s always going to have a critique, someone’s always going to have some negativity to say about me. So, all that matters is what I think of it.”

Lizzo

The singer continued, “And I had to go so deep inside myself and look in the mirror. Looking in the mirror and accepting what’s in the mirror is very, very difficult. And right now, I love it every time I look in the mirror.”

Jennifer Lawrence

Jennifer Lawrence is a human being, so she sometimes sees herself inaccurately, as we all do. Whether that’s claiming that she’s the first female action star (she’s not) or that she’s paid less than her male counterparts (that’s true, but it’s not something normal people with ordinary salaries would think of as a big issue).

Jennifer Lawrence

Well, another example is Lawrence talking about how overweight she is, even though she isn’t. The actress has said, “In Hollywood, I’m obese. I’m considered a fat actress.” Well, at least she’s confident about her imaginary fat.

Serena Williams

People often seem to be confused as to why Serena Williams is famous. Williams is a tennis player, so of course, she isn’t going to have the same body type as a runway model. Hollywood likes all its celebrities to look a certain way, though, so Serena’s athletic figure is often the subject of scrutiny.

Serena Williams

Williams, however, made it clear that her body does exactly what it needs to. She said, “I’m really happy with my body type, and I’m really proud of it. Obviously, it works out for me.”

Amber Riley

Before she found fame with Glee, Amber Riley auditioned for American Idol but got rejected. Some believe the decision was due to her size, although that hasn’t been confirmed or denied by production.

Amber Riley

Ironically, Riley returned to American Idol not as a contestant, but as a guest performer with the rest of the Glee cast. Amber recalled the incident, saying, “I had the full circle moment of realizing like it, it wasn’t that you weren’t good enough. It just wasn’t your time yet.”

Kelly Clarkson

Having found fame through a reality show rather than the traditional Hollywood channels, Kelly Clarkson doesn’t look like the typical singer who gets signed by a big record label. Clarkson has been open about producers pressuring her to go on a diet and magazines altering her photos.

Kelly Clarkson

Kelly herself has no issues with her body though. The singer has said, “If you gauge your life on what other people think, you’re going to be in a constant state of panic trying to please everyone.”

Meghan Trainor

Given that her first hit single was the body-positive song “All About That Bass”, it’s no surprise that Meghan Trainor is a big believer in loving one’s figure — regardless of size.

Meghan Trainor

Trainor spoke about the tune that made her famous by saying, “It was a song for myself about my body insecurities.” She also advised, “We should all have a big banner, or maybe a neon sign, in our bedrooms: Every inch of you is perfect.”

Cardi B

Cardi B’s appearance has changed quite dramatically over the years, as she had some cosmetic work done — and then undone when she suffered complications from the procedures. Nowadays, the rapper is learning to love and accept her body as it is, rather than risking her health to chase beauty standards.

Cardi B

Cardi apparently thought she was being unique when she said, “I like being perfect.” She either feels she’s reached that goal or that it’s no longer worth it, as she’s since announced, “I ain’t getting surgery again.”

Beyoncé

Beyoncé is one of the pop stars who changed the beauty standards game. Relatable hits like “Bootylicious” bought Queen Bey a lot of credit to make up for whatever her newer music is. It’s not just Beyoncé’s art that’s changed, but also her concern with being a certain weight.

Beyoncé

The singer has said, “My health, the way I feel when I wake up in the morning, my peace of mind, the number of times I smile, what I’m feeding my mind and my body — those are the things that I’ve been focusing on.”

Post Malone

In 2023, fans were hardly able to recognize Post Malone after his dramatic weight loss. A little less than a year prior, the singer announced that he’d be making some lifestyle changes while anticipating the birth of his first baby.

Post Malone

Post Malone declared, “Time to take care of my body and my family and friends, and spread as much love as we can every day.” Perhaps that’s where this change has come from? However Postie wants to show up, we’re here for it!

Halsey

Halsey provided a service to women everywhere when she clarified that how she looked shortly after giving birth wasn’t a standard that every new mother needs to reach. The singer explained, “The body behind all those compliments the other night was wearing a custom-tailored outfit and lighted perfectly after much testing, so I could feel good and do my job.”

Halsey

The star continued, “I do not want to feed the Illusion that you’re meant to feel and look ‘great’ immediately postpartum. That is not my narrative currently.” Thanks for keeping it real, Halsey!

Jennifer Lopez

When she was first starting out in Hollywood, Jennifer Lopez’s team begged the singer/actress to lose weight. Lopez held strong, though, and ironically her curves are a big part of what’s made her so famous.

Jennifer Lopez

JLo explained that such confidence often starts at home. She said, “My dad loved my mom’s body — all the men in our family loved the women’s bodies. […] And so, later on, when I brought that in front of the world, I wasn’t really trying to send a message. I was just being myself.”

Gigi Hadid

Gigi Hadid had a tough time becoming an established model because she “didn’t have a runway body.” Hadid gave into the pressure — no judgment, we’d probably do the same — but she’s now at a point in her career in which she no longer has to play by the rules.

Gigi Hadid

Perhaps she’ll try to get her old figure back? The model has confessed, “It was a body that I loved. I knew how hard I worked to have those muscles, to be curved in those places – I kind of miss it now.”

Bella Hadid

After getting a nose job that she’s come to regret, Bella Hadid has learned to love and accept her body exactly as it is. The model has said, “I’ve really learned that beauty for me is about that confidence within. And being able to work on your mental health.”

Bella Hadid

The model continued, “I look at my body now as a temple. Before, it kind of got to the point where my body wasn’t owned by me. Now I feel like I own my body again.”

Madonna

Madonna has had a lot of cosmetic procedures lately, which is obviously fine and well since it’s her face. The confusing part is that she calls people “ageist” when they’re exhibiting the opposite behavior by saying they’d love to see the Queen of Pop age naturally.

Madonna

Madonna announced, “I have never apologized for any of the creative choices I have made nor the way that I look or dress and I’m not going to start.” Nor should you! But also, please recognize that there’s nothing ageist about people advocating for aging naturally.

Ariana Grande

Ariana Grande has expressed concern for her young fans, given the pressure even non-celebs have to always look perfect. The singer wants to teach young women the same confidence her mother taught her.

Ariana Grande

Grande has said, “I think the thing that I want to instill in them most is [the message that] you are loved, and there are so many different kinds of beautiful. You are beautiful today if you have 10 cupcakes, and beautiful tomorrow if you do a juice cleanse. You’re beautiful because of who you are.”

Iggy Azalea

Iggy Azalea was all of us when she said, “Some days I just think I want to crawl in my cave and I don’t feel confident at all, and other days I feel great.”

Iggy Azalea

The rapper keeps her self-esteem up and her body healthy by exercising several times a week and eating a diet that restricts processed foods, carbs, and sugar. Of course, Azalea has had the help of cosmetic procedures too, but she’s always been honest about it.

Nicki Minaj

Nicki Minaj has expressed that she regrets the cosmetic work she’s had done on her backside, but at the time, she felt it was necessary for her career.

Nicki Minaj

Minaj explained, “All I would hear them talking about is big butts and I didn’t feel complete or good enough, good as those girls because I’m like ‘Oh my god, you know, this is what you’re supposed to look like in the rap culture and I don’t look like that.’” It seems that since her comeback, Nicki has embraced her natural figure.

Khloé Kardashian

Khloé Kardashian has suffered a lot of criticism due to her cosmetic procedures and photo editing, both of which are common practices within the Kardashian clan. However, the reality star has made it clear that she’s confident in her methods and doesn’t plan to change her ways.

Khloé Kardashian

Khloé said, “My body, my image, and how I choose to look and what I want to share is my choice. It’s not for anyone to decide or judge what is acceptable or not anymore.”

Megan Thee Stallion

Megan Thee Stallion is beloved by fans for posting relatable photos on social media, including some of her cellulite. The rapper made sure that no one has to wonder how she feels about her body when she took the time in one of her concerts to say, “I don’t know about y’all but I love my body.”

Megan Thee Stallion

The star also exclaimed, “I do what I want to my body with who I want to with my body… if you love your body let me hear you make some noise.” Message received!

Dua Lipa

Although Dua Lipa meets Hollywood’s standards of the ideal body type, she’s still a human being and, therefore, has some insecurities about how she looks. However, the singer has a method to help herself feel confident each day.

Dua Lipa

Dua advises her fans, “I do feel quite confident in my body, there’s always going to be something you don’t like, but it’s so much healthier to tell yourself two things you like about yourself every day.”

Cher

At the time of writing, Cher is in her 70s but can still outlast a woman half her age at the gym. The singer admits that she works “twice as hard” to maintain her body these days, but is happy with the results.

Cher

Cher exercises, eats healthy, and takes care of her overall well-being. She believes that having her body type at a later age is that simple. Cher said, “I’ve killed myself in the gym to have this body. It isn’t like I have some amazing secret that nobody else has.”

Kate Hudson

Kate Hudson feels that, as a celebrity, she has a certain responsibility to her young fans. The actress has said, “If there is one thing I will never have, it is an eating disorder. […] Because it is a serious sickness, not something to plaster on the cover of a magazine.”

Kate Hudson

She has also expressed, “I’m pretty comfortable with my body. I’m imperfect. The imperfections are there. People are going to see them, but I take the view you only live once.” Finally, usage of the term YOLO we can actually get behind!

Tyra Banks

Over time, Tyra Banks has turned from runway model to full-on businesswoman, while having all sorts of careers in between. Naturally, as her roles change, so does the need to have a certain body type.

Tyra Banks

Banks is no longer required to have a model’s physique to do the work she’s currently doing (whether or not anyone should be compelled to have a model-esque body type for any job is an argument for another day). Tyra has proudly declared that, nowadays, “My body is fuller. And so is my mind.”

Jesy Nelson

Former Little Mix member Jesy Nelson cites body image issues as one of the reasons that she left the girl group. While a solo career hasn’t solved all of Nelson’s problems, she does feel that it was the right move for her.

Jesy Nelson

The singer says she’s been able to improve her confidence now that she’s no longer being compared to her former colleagues. Nowadays, Jesy says she’s “embracing the little pot chubs belly and I just love it.”

Christina Aguilera

Christina Aguilera has been in the public eye since she was nine years old. Naturally, her body has gone through many changes — after all, no one looks the same at 40 as they did at 20. Aguilera has found herself the subject of criticism when she dared to age and put on a few pounds, rather than be forever 25.

Christina Aguilera

The singer let everyone know exactly what she thinks of their judgment when she said, “As long as I’m happy in my own skin, that’s all I need, that’s all the confirmation I need.”

Amy Schumer

Amy Schumer isn’t a size zero. So, naturally, Hollywood tried to pressure her into losing weight. At first, Schumer complied but, according to her, she doesn’t look good slim — and the change didn’t last.

Amy Schumer

These days, the comedian is happy at her current weight and has the star power to ignore anyone who tries to change her. Amy has said, “I feel very good in my own skin. I feel strong. I feel healthy. I do.”

Lena Dunham

Lena Dunham doesn’t care about fitting into Hollywood’s idea of what a celebrity should look like. The actress showed her lack of concern with public opinion when she said, “Now I’m able to very proudly be in the body I’m in, recognizing what it’s taken to get here.”

Lena Dunham

Dunham continued, “I weigh the most I ever have, I love the most I ever have. I read and write and laugh the most I ever have. And I’m the happiest I’ve ever been.”

DJ Khaled

DJ Khaled knows that he’s not necessarily the most chiseled guy in the room, but he’s also not going to join the body-bashing brigade. The producer has said, “I’m not the slimmest guy — I’m not the biggest guy, but I don’t got a six-pack. But at the same time, I look in the mirror and I’m like, ‘Man, I’m gorgeous, I’m beautiful.’”

DJ Khaled

Who else finds this neutral perspective refreshing? It’s pretty ironic that we’re getting such a grounded analysis from a guy who gets paid to scream “We the best!”

Camila Cabello

Camila Cabello has received a lot of criticism for looking different now than she did in her Fifth Harmony days. Apparently, she’s supposed to look exactly the same after all these years.

Camila Cabello

Cabello spoke out about the media’s commentary on her beach body by saying, “Being at war with your body is so last season. We are real women, with curves, and cellulite, and stretch marks, and fat.” Name us a woman who doesn’t naturally have those things — we’ll wait.

Celebrities Who Dated Before They Were Famous

By Thalia Shepherd – 3/23/20

George Clooney & Kelly Preston

Everyone was dating everyone in the 80s, including George Clooney and Kelly Preston. Dating for two years, neither had found any major success in either film or television. In fact, it would be about five years before Clooney would stop hearts on the highly acclaimed television show, ER. During these two years of relationship, they lived together, as well, but they eventually decided that it was better to go their own ways. This ended up being fine, as both wound up having a good career and finding their true love.

George Clooney & Kelly Preston

Reese Witherspoon & Chris O’Donnell

Reese Witherspoon may be a big star now, but in the early 90s, she was just getting her feet wet. However her beau, Chris O’Donnell had already begun to climb the ladder with films like Scent of a Woman and School Ties. The two would date for a while before both reaching the top of their mountains. Reese would go on to star in Pleasantville and Cruel Intentions, which would launch her into stardom. Meanwhile, Chris would try his hand at superhero movies and eventually find acclaim in Batman & Robin.

Reese Witherspoon & Chris O’Donnell

Joey Lawrence & Keri Russell

This relationship may have been doomed from the start, but it was the talk of the town in the 90s. Joey Lawrence was about to be a household name as the cool but not so intelligent brother of Blossom. Meanwhile, his partner hadn’t quite reached the height of her fame as Felicity. The relationship was sweet but couldn’t last because Keri was still seeing her Mickey Mouse Club co-star, Tony Lucca.

Joey Lawrence & Keri Russell

Liam Neeson & Helen Mirren

Both of these stars have been acting for much longer than they have been household names. They met while filming the Oscar-nominated Excalibur. Meeting on set in 1981, Nelson fancied Mirren and they soon began dating. The couple dated and lived together for five years before splitting up. The two actors would go on to find fame long after their break up. They discussed it on the British talk show, Graham Norton, in 2018, and the revelation shocked many people.

Liam Neeson & Helen Mirren

Justin Timberlake & Jenna Dewan

This short-lived couple dated a while back. When Justin Timberlake decided to go solo, he would have to prove himself all over again. At the same time, Jenna Dewan was trying to make a name for herself in the dance world. She signed up to be a backup dancer for the newly solo Justin. The two hit it off and dated briefly but realized they were better as friends and parted ways amicably.

Justin Timberlake & Jenna Dewan

Tobey Maguire & Rashida Jones

Maguire wouldn’t hit it big until he donned the spandex and flew around New York City as everyone’s friendly neighborhood Spiderman. Before this, the two stars had a three-year relationship. Jones would go on to become a star as a member of the cast of Parks and Rec. Meanwhile, Maguire would do a three-movie stint as the web-slinger and move on to other hits, such as Seabiscuit.

Tobey Maguire & Rashida Jones

Lisa Kudrow & Conan O’Brien

Can you believe that Lisa Kudrow was once shy? When she and O’Brien met in an improv class, she certainly was. That didn’t stop her from being smitten with the ginger late-night talk show host, though. These two very funny individuals would carve out a name for themselves in two very different ways, but they still found their path to stardom. They dated briefly before deciding to just be friends.

Lisa Kudrow & Conan O’Brien

Jessica Simpson & Jensen Ackles

Jessica Simpson’s love life is no secret. Many of her relationships played out in the public eye, but one that most may not know about is the one with the star of Supernatural. Long before both were household names, the two were an up and coming it-couple. After dating for about a year, the two split after Ackles allegedly cheated on her with his next famous girlfriend, Leann Rimes.

Jessica Simpson & Jensen Ackles

Ryan Gosling & Sandra Bullock

Bullock was already a star, having starred in films like Speed and Miss Congeniality, but Gosling only had a few credits under his belt. The two met while filming the thriller, Murder by Numbers, in 2002, and the sparks flew instantaneously. The couple would let everyone know about their relationship on the red carpet of the movie’s premiere. Dating for just a short time, the two eventually went their separate ways, but neither have anything bad to say about each other. Gosling would go on to become a star and one of the biggest Hollywood heartthrobs of recent history.

Ryan Gosling & Sandra Bullock

Adrien Brody & Elsa Pataky

Adrien Brody had already won an Oscar for his role in the film The Pianist, but Elsa was relatively unknown unless you watch Spanish films. Eventually, she would break through and become pretty well-known through her part in the Fast & Furious franchise. The two dated back in 2006, and Brody was so much in love that he bought his girl a castle. Eventually, they would break up and Pataky went on to marry her now-husband Chris Hemsworth.

Adrien Brody & Elsa Pataky

Katy Perry & Matthew Thiessen

Katy Perry started in the Christian music world, which makes it easy to understand how she could find herself dating the lead man of Relient K. The two dated for three years, and during that time, it wasn’t strange to find Perry at the concert stage diving and having a good time. In 2005, the couple would call it quits. Just two years later, Perry would become a huge pop star while Thiessen remained pretty popular himself.

Katy Perry & Matthew Thiessen

Ryan Reynolds & Melissa Joan Hart

Melissa Joan Hart had already cemented her name in the teen drama genre as Clarissa in Clarissa Explains It All. Reynolds, on the other hand, hadn’t quite found his groove. Even still, they met on the set of the movie that would launch the long-running television show Sabrina the Teenage Witch. They were very attracted to each other and dated for a bit, but Hart was still involved with another guy, so it didn’t go very far. They would split up, and several years later, Reynolds would make his mark on Hollywood.

Ryan Reynolds & Melissa Joan Hart

Sofia Vergara & Enrique Iglesias

Iglesias was born into stardom and had already made quite the name for himself when he began dating Sofia. As Sofia began to break into American television (she was already well-known in Colombia), she found solace in the arms of the sexy Latin pop star. They were very attracted to each other and dated for a bit, but Hart was still involved with another guy, so it didn’t go very far. They would split up, and several years later, Reynolds would make his mark on Hollywood.

Sofia Vergara & Enrique Iglesias

Drew Barrymore & Corey Feldman

The two had been on a date years before they got involved, according to Feldman. Set up when they were just 10 and 14, the two didn’t hit it off until they worked together on an after school special. The two would date only a little while and would eventually end it in 1989. Barrymore had begun the process of getting sober and Feldman was still in the midst of substance abuse. The relationship just couldn’t work.

Drew Barrymore & Corey Feldman

Sarah Jessica Parker & Robert Downey Jr.

In 1984, Downey Jr. and Parker would work together on a drama called Firstborn. Working closely together, the two would fall head over heels for each other and the rest, as they say, is history. The two would date for 8 years before separating. The relationship ended with Downey Jr.’s battle with addiction. Downey would eventually kick the problem after several run-ins with the authorities. He then suited up in his now-iconic defining role…Iron Man. Parker would eventually find love with Matthew Broderick and fame as Carrie on Sex in the City.

Sarah Jessica Parker & Robert Downey Jr.

Busy Phillips & Colin Hanks

Busy Phillips would find her footing on the hit series Freaks and Geeks. Colin Hanks (son of the famous actor, Tom Hanks) would get his foot in the door on the teen sci-fi drama, Roswell. Before all of that, though, both of these actors went to college together, and that is where they fell for each other. After dating all through college, they would eventually break up. Though their romantic love faded, their friendship did not. The couple is still close, even taking vacations together with their spouses.

Busy Phillips & Colin Hanks

Jessica Biel & Chris Evans

Jessica had already seen her star rise on the family drama 7th Heaven, but Chris hadn’t yet found his place in the Hollywood rat race. The two dated off and on throughout a four-year time frame from 2001-2005. Both of these stars would go on to find success, both on the big screen and on the small. Much like Robert Downey Jr., Chris would come into his own fame by slipping on a superhero costume. The red, white, and blue spandex of Captain America would go on to make Chris Evans a household name.

Jessica Biel & Chris Evans

Zooey Deschanel & Jason Schwartzman

This pair broke up in 2005 after having started to date six years before. When they started dating, Jason had just made a small impression in his hit movie, Rushmore. However, Zooey had not yet made her big debut in Almost Famous. Deschanel would go on to find even more fame on New Girl, which had its series finale in 2018. Likewise, Schwartzman would find even more acclaim in movies such as The Grand Budapest Hotel and Wine Country.

Zooey Deschanel & Jason Schwartzman

Fred Savage & Jennifer Love Hewitt

This didn’t spring a fling, but these two did have a date — in fact, Savage was Hewitt’s first date. The two would spend the evening at the Laugh Factory, but that would be the first and final date. It seems that Savage was a little weirded out by Hewitt’s pet pig and just couldn’t bring himself to give her a second date. Though Savage was very well-known at the time, Hewitt hadn’t quite made it. She would find fame on shows like Party of Five and in movies such as I Know What You Did Last Summer.

Fred Savage & Jennifer Love Hewitt

Justin Timberlake & Fergie

Before these two mega pop stars even made it onto the billboard charts, the two icons dated. In 1997, Justin and NSYNC hadn’t even released their first album and Fergie was still part of the girl group Wild Orchid. However, the two found time to date a little. The relationship wouldn’t last long, but that is okay because they still have mad respect for each other and have each found love.

Justin Timberlake & Fergie

Charlie Sheen & Robin Wright

Most of Charlie Sheen’s failed relationships are all part of the public record, but this one has been kept under the rug for quite some time. It seems that the two future stars dated in the early 80s. As a teenage fling, this relationship would last just a year. Each of the two stars would move on and make their marks in both film and television. They would also move on to find and lose love with other celebrities like Denise Richards and Sean Penn.

Charlie Sheen & Robin Wright

Juliette Lewis & Brad Pitt

These two met on the set of Too Young to Die. The two began dating and would do so for four years. There was a big age difference, but that didn’t seem to matter. In 1993, they would break up and move on to more high profile roles and relationships. Lewis would star in acclaimed films like Natural Born Killers, and Pitt would go on to be one of the hottest and most sought after actors in Hollywood.

Juliette Lewis & Brad Pitt

Miley Cyrus & Tyler Posey

This was puppy love from the very beginning. The innocent relationship sprung up after Posey starred in a show with Cyrus’s dad called Doc. The two were nine and seven, so it was the hold hands, kiss on cheek kind of romance, but it still counts as dating! Cyrus would go on to star in Hannah Montana and carve out a place in both film and music for herself. It would be many more years before Posey would find his light and star in the MTV teen supernatural drama Teen Wolf.

Miley Cyrus & Tyler Posey

Neil Patrick Harris & Christine Taylor

Neil Patrick Harris had gained some fame with his role as Doogie Howser, and Christine Taylor shined her star just a bit in the Very Brady Movie. However, neither had gained big fame when they dated in 1997. The couple split when Harris realized that he loved her, but just not in that way. In fact, Harris realized that perhaps there was a reason for this and would eventually come out publicly in 2006.

Neil Patrick Harris & Christine Taylor

Jennifer Garner & Scott Foley

Foley was already a rising star with his role on Felicity, and that is where this pair met. Garner played his girlfriend, and they instantly connected. Eventually, Garner would also go on to be a rising star with her hit show Alias. They would eventually marry in 2000 but would divorce just three short years later in 2003. Garner has gone on record saying that if they had not been in Hollywood, the relationship would have lasted much longer.

Jennifer Garner & Scott Foley

David Gallagher & Megan Fox

Both had a modicum of celebrity, but neither were the stars they were set to become. Fox and Gallagher dated for quite awhile in 2003 and were thick as thieves the whole time. Like many young loves, the romance just faded and they eventually would split up. Megan would go on to star in Transformers and marry Brian Austin Greene. Gallagher has continued to work in television and has faded a little from the limelight.

David Gallagher & Megan Fox

Matthew Morrison & Kristin Bell

Meeting at college, these future television stars hadn’t even graduated when they dated for a short period. Eventually, the duo would make their mark on Hollywood, but not before splitting up. Bell would go on to star in Veronica Mars, a role she recently reprised, and she would voice Anna in the very popular Frozen movies. While Bell was doing that, Morrison headed to Broadway and started building the reputation that would eventually land him his role on the hit show, Glee.

Matthew Morrison & Kristin Bell

Scarlett Johansson & Jack Antonoff

Now both stars in their field, these two dated for a while in high school. The relationship would last two years. They would eventually break up as Scarlett moved on to the rat race of Hollywood, breaking Jack’s heart. Now, Antonoff is a very successful music producer, and Scarlett is one of the most famous actresses in the world. It took time, but they both got over the heartbreak and moved on.

Scarlett Johansson & Jack Antonoff

Leighton Meester & Sebastian Stan

This Gossip Girl couple dated for two years and kept the entire thing pretty much out of the paparazzi’s camera lens. This relationship started as an on-screen one and morphed into a real-life one in 2008. Now, Antonoff is a very successful music producer, and Scarlett is one of the most famous actresses in the world. It took time, but they both got over the heartbreak and moved on.

Leighton Meester & Sebastian Stan

Jennifer Love Hewitt & Will Friedle

Jennifer Love Hewitt had a string of teen romantic comedies in the 90s, and one of these was Trojan War. This is where she and Friedle hit it off and found that there was a spark. They began dating while filming the movie in 1997, though they had been introduced before this. Hewitt would elevate her star status over the next decade. Meanwhile, Friedle would leave his mark with voiceover work, such as Ron Stoppable in the Disney animated show, Kim Possible.

Jennifer Love Hewitt & Will Friedle

Matthew Morrison and Lea Michele

Before Glee became popular, it turns out Matthew Morrison had a thing for Lea Michele. This was confirmed by Lea in an excerpt from her book after a long time of rumors. Back in 2010, Michele claimed that the two had been friends for a long time, while later on, Morrison claimed the romance reports as downright “laughable.” It seems that Morrison and Michele dated for a hot minute back in the day when the Fox show was nothing but a glimmer of what it turned out to be.

Matthew Morrison and Lea Michele

William H. Macy and Felicity Huffman

Felicity Huffman and William H. Macy make up one of the great celebrity couples, with more than 20 years of marriage. Their long relationship started back in the 1980s, where they met at the Atlantic Theater Company. After 15 years of dating, Felicity finally accepted his proposal to become his wife. Despite their on-and-off relationship, they are happy to this day, with no end in sight!

William H. Macy and Felicity Huffman

Ashton Kutcher and January Jones

One of our all-time favorite couples might be Kutcher and Jones, as it’s impossible not to love them for their fashionable styles. They started dating in the late 1990s when she was known for being a model. It is unsure how they met, but their relationship dissolved in the early 2000s. Jones claimed that the guy she was dating back then was not really supportive of her acting career, so she decided to go her separate way.

Ashton Kutcher and January Jones

Angela Bassett and Courtney B. Vance

This couple not only has ageless looks but also a rock-solid relationship that dominated the red carpet for many years. When the two met back in the 1980s at an elite drama school, there was no spark that set them off. In fact, Vance was dating someone else at the time. After many years of friendship, nothing happened…until 14 years later. In 1994, the couple went on a date, but nothing memorable happened until later when something just clicked!

Angela Bassett and Courtney B. Vance

Carey Mulligan and Marcus Mumford

A heart-melting story is that of Carey and Marcus. They used to be pen pals back in their childhood but lost touch over time. They reconnected as adults, and the two are now married and have been since 2012. Their romance seems to be taken from a book – the couple never forgot how they started, and they still write love letters to each other. What a real love story for a hopeless romantic!

Carey Mulligan and Marcus Mumford

Jon Hamm and Jennifer Westfeldt

Despite a painful end, Jon Hamm dated actress Westfeldt from 1997 to 2015. They never got married, but they had been life partners before becoming famous. Although the rumor mill is still spinning, leaving us only to wonder, some claim that the breakup had something to do with Hamm’s admission to rehab. This also coincided with Mad Men’s finish date in 2015.

Jon Hamm and Jennifer Westfeldt

Alanis Morissette and Ryan Reynolds

These two lovebirds had a pure romantic encounter that some might find a little quirky. They met at Drew Barrymore’s birthday party in 2002. Two years later, the duo was engaged. What makes them so quirky? Here are some statements Alanis made about her fiancé, “[she felt so loved by him], in a trampoline kind of way.” Are you not convinced yet? Here is another one, “He is like a soul brother to me, except that I want to jump his bones.”

Alanis Morissette and Ryan Reynolds

Robin Thicke and Paula Patton

Paula met Robin back in 1991 when they were both teenagers. She recalls him asking her to dance, and the rest followed naturally. In 2005, after many trials, the couple got married. They then welcomed a son in 2010. Only three years later, the waters started to become cloudy. Thicke’s questionable behavior was one factor that put the couple under the microscope. Shortly after that, in 2014, Thicke and Patton decided to part ways.

Robin Thicke and Paula Patton

Jay Leno and Sharon Osbourne

Sometime in 1978, a secret fling took place between Jay Leno and Sharon Osbourne. This only came to public knowledge in 2013! When she was 25 and moved to America, Sharon went to a club, where she met Leno while he was performing his usual comedy routine. She prank called him with her friend, and since he liked her voice, they met and had “a little fling!” Leno was, in fact, in love with someone else, and he introduced Sharon to his love shortly after that, showing her the town.

Jay Leno and Sharon Osbourne

Oprah Winfrey and Stedman Graham

Another winning couple that withstands the test of time is Oprah Winfrey and Stedman Graham. When asked about their situation, they describe it as a spiritual partnership. They first met in 1986, while attending a charity event. What is impressive is that Winfrey and Graham are not married! She believed that their relationship would change if they wed, and she is convinced that they would have broken up if they had decided to get married.

Oprah Winfrey and Stedman Graham

Michael Keaton & Courtney Cox

Michael Keaton had just arrived in Hollywood in the early 80s and soon found himself dating a fellow up-and-coming actor. Cox and Keaton dated for six years and finally split not long after Cox found her place in a wacky group of friends. Each went on to do great things both in film and television, as well as find their true love.

Michael Keaton & Courtney Cox

Minka Kelly & Donald Faison

Faison was already quite well-known for his role in Scrubs when the two began dating. Kelly, however, still had a little time to wait before she became a star. After a year of dating, the couple split in 2005. Both have continued to make their name in the film and television industry, and they both have continued to turn heads with their relationships.

Minka Kelly & Donald Faison

Keira Knightley & Jamie Dornan

In 2003, Keira Knightley had just begun her rise to fame after starring in the movie Bend It Like Beckham, and Jamie Dornan was just a Calvin Klein model. The duo would meet and fall hard for each other. After dating for two years, the pair split up in 2005. Knightley would keep working, finding her stride with films like the Pirates of the Caribbean franchise and several period pieces. Whereas Jamie would eventually get a film credit to his name in 2006 and work his way up to being cast as the lead in the Fifty Shades of Grey movies.

Keira Knightley & Jamie Dornan

Jennifer Grey & Matthew Broderick

Long before Baby couldn’t be put in the corner and Ferris took his day off, this couple dated and was deeply in love. In 1987, the couple got into a car crash and that is how the fact that they were dating came to light. After this happened, the two parted ways, as the relationship took a major hit with this awful accident. The two would go on to date others, and for Matthew, he would find love with another person on our list, Sarah Jessica Parker.

Jennifer Grey & Matthew Broderick

Denise Richards & Paul Walker

Paul Walker came to fame in the Fast & Furious franchise and sadly passed away in an automobile accident. Before he became famous, he dated some other soon-to-be-famous people. One of those relationships came from his stint on a 1994 movie called Tammy and the T-Rex. The movie may have been a dud, but Paul certainly found solace in the arms of his costar, Denise Richards. The couple dated for a little while and then separated shortly after.

Denise Richards & Paul Walker

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