Most celebrity romances capture exciting headlines, from the glamorous Hollywood love stories to affairs and scandals. Just as there will be those to remember for talent, others will be remembered for their colorful histories in the dating scene. Many celebrities enter the complicated web of relationships by dating several women, from fellow entertainers, models, and social media influencers.
Their love lives remain bright under the spotlight of media attention; their every new romance breaks the news for the day. These celebrity romance love stories open windows into celebrity romance's bright yet often murky world. Here are 20 celebrities with high-profile long-term dating histories and the women they dated.
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1) Leonardo DiCaprio
Leonardo DiCaprio is known for appearing in films like Titanic and The Revenant. His list of romantic relationships is impressive, including models and actresses like Gisele Bündchen and Bar Refaeli, which naturally attracted considerable public attention due to the significant age gap.
His most recent girlfriend was Camila Morrone, and that was huge news concerning their age gap. DiCaprio's love life perfectly symbolizes Hollywood's obsessive charm with beauty and youth because here is this guy who is still highly in demand both on-screen and off.
2) John Mayer
Besides his music career, John Mayer is known for his love affairs with Hollywood stars from Jennifer Aniston to Katy Perry and Taylor Swift. His love life has topped headlines and most of his candid lyrics come as the truth about his real life.
He is now a studio genius and an attraction for the ladies. The boyfriend, though, is one prized with an end because criticisms have bombarded him with all sorts of beatification in his past talking about exes. Throughout the years, Mayer has developed and matured about his relationship life, it seems he is looking for deeper connections.
3) George Clooney
George Clooney's dating history is one thing of a laundry list of significant-name relationships boasting his wit and sense of humor. But before marrying Amal Alamuddin in 2014, the actor dated many actresses and models. He was also rumored to pursue Kelly Preston in the late '80s and even steady with Lisa Snowdon in the early 2000s.
Clooney had also been pretty serious with other celebrities, such as Elisabetta Canalis and Stacy Keibler, apart from his affair with Bar Refaeli. His reputation as a Hollywood bachelor was finally written in stone when he vowed never to get married until he met Amal Alamuddin, a human rights lawyer who impressed him not just with her intelligence but also with her activism, and to whom he got married and had their twins in 2017.
4) Justin Bieber
The media always spots Justin Bieber's romantic life, especially when he enters the list of high-profile ones. It is the most recorded romance for Selena Gomez from 2010 until 2018. To the amazement of his fans, their on-and-off relationship captured much attention, playing a major influence on both music careers.
After his dalliance with Gomez, Bieber dated Hailey Baldwin in passing in 2016 and rekindled the romance in 2018. The relationship heated up enough that he proposed to her in July of that year. They got married in a courthouse in October, and he is reportedly throwing a bigger bash for them in 2019.
5) Harry Styles
Besides music, Harry Styles has always been known for his extra-romantic relationships with many female celebrities, which draws media attention. Many are aware of his relationship with Taylor Swift in 2012, an affair that certainly drew public interest and inspired much of Swift's subsequent music.
Another notable relationship is with Kendall Jenner, whom he has been associated with on several occasions and whose romance was widely rumored to be on and off again. Other important relationships he was seen with include model Camille Rowe, whom he had been in for nearly a year. Sources reportedly say she inspired some of the songs on Fine Line.
6) Drew Barrymore
Drew Barrymore is regarded as one of the great American actresses, producers, directors, and talk show hosts with effortless varieties of infectious energy on film. Besides the shrieks of criticisms and controversies barraging her personal life, she has been herself. She has been married three times to a bartender named Jeremy Thomas, then to comedian Tom Green, and then to Will Kopelman, with whom she has two daughters.
Blending this saga of love and relationships with her rise to fame and addiction and recovery battles made her one of the most apologetically candid stars of recent times, rarely hiding the truth of her life.
7) Matthew Perry
Matthew Perry's personal love life often hit the headlines, mainly whenever it involved different actresses. Among the most highlighted affairs he was involved in was with Julia Roberts, whom he was alleged to have been in an affair with during the early years of the 1990s. He met Julia Roberts when she guest-starred on Friends during the show's second season in 1995. The episode The One After the Superbowl became a showcase of their chemistry, helping push the show to such great heights of popularity.
Perry and Roberts had barely been dating for some time, but they still got a lot of attention in the media because both were superstars during their relationship. They were constant photographic partners at all events, and people would call them the perfect Hollywood power couple.
8) Rihanna
RiRi has had several high-profile relationships within her lifetime. The most publicized relationship she ever had was with singer Chris Brown, with whom she had an on-and-off relationship between 2007 and 2009 that ended after a much-publicized incident of domestic violence.
Later, Rihanna dated baseball star Matt Kemp in 2010 and also had her share of romantic involvement with rapper Drake on and off from 2009 to 2016, frequently feeding gossip sites through featured collaborations.
Rihanna dated the Saudi businessman Hassan Jameel from 2017 to 2020, and their romance was kept private. In 2021, she publicly announced her relationship with the American rapper A$AP Rocky. She has had two children from him, one in May 2022 and another in 2023.
9) Drake
Several high-profile relationships and dating rumors are observed throughout his relationship history. He dated Rihanna and had an on-again-off-again relationship with the singer between 2009 and 2016. He was also rumored to be dating Jennifer Lopez at the beginning of 2017. Then, there was a relationship with model Johanna Leia in 2021.
There are many stories regarding flirtations between Drake and female celebrities; however, he usually avoids publicity surrounding his private life, so he hasn't made a public long-term relationship lately.
10) Kanye West
Among Kanye West's high-profile relationships, he dated designer Alexis Phifer, with whom he was engaged from 2006 to 2008. He then dated model Amber Rose between 2008 and 2010. In 2012, West dated reality star Kim Kardashian, and then to each other; they got married in 2014 and became the most talked-about celebrity couple. They have four children together and divorced recently in 2021.
Since their split from Kardashian, West has been reported to have been in a relationship with model Irina Shayk in 2021 and also dated actress Julia Fox sometime in early 2022. He married Bianca Censori in 2022.
11) Calvin Harris
Among the most discussed is Calvin Harris's relationship with singer Rita Ora, whom he dated from 2013 through 2014 on rather bumpy terms. The Scottish DJ/music producer afterward dated model Aarika Wolf off and on several years later.
His most publicized connection was with pop diva Taylor Swift, whom he dated from 2015 to 2016. The end of the relationship became news because of the rumors about her immediately getting close to the most handsome Englishman on the screen in Hollywood, British actor Tom Hiddleston, famous for roles such as Loki in the Marvel Studios franchise.
Harris dated singer Tinashe briefly in 2016 and then dated Aarika Wolf from 2018 through 2022. In 2023, he married British TV presenter Vick Hope in a much more private, long-term relationship.
12) Pete Davidson
Most recently, Pete Davidson has been topping headlines for dating comedian Carly Aquilino. Before that, he dated actress Cazzie David between 2016 and 2018.
However, Pete Davidson's most-publicized relationship was with pop star Ariana Grande, whom he started dating in 2018 and briefly became engaged to, though they broke up the same year. In early 2019, he was reportedly dating actress Kate Beckinsale. He then reportedly dated actress Margaret Qualley for a couple of months later that year.
13) Zac Efron
Zac Efron has been known to have several high-profile relationships dating back. Among the most famous is his High School Musical co-star Vanessa Hudgens. He dated the actress from 2006 to 2010. Since his split from Hudgens, Efron was pictured with actress Lily Collins and model Sami Miró, whom he reportedly has been dating for nearly two years, from 2014 to 2016.
Recently, he's been rumored to be dating Australian model Vanessa Valladares during his short stint in Australia in 2020 during the pandemic. However private Efron may attempt to be, relationships like these come to mainstream light.
14) Ben Affleck
Being Ben Affleck means having a few pretty high-profile romances with various actresses. Among these dates in his life is Gwyneth Paltrow; he dated her early in the 2000s, on and off for a few years. He married Jennifer Lopez in 2002, called off the wedding in 2003, and divorced in 2004.
Affleck married actress Jennifer Garner in 2005, with whom he had three children, before divorcing her in 2018. He has dated several women since his divorce from Garner, including Saturday Night Live producer Lindsay Shookus and actress Ana de Armas. In 2021, Affleck married Jennifer Lopez, whom he married in 2022.
15) Usher
Usher's romantic past would seem more glamorous and complicated than anyone would imagine, considering his status as one of R&B's biggest stars. He is known for a very long-term relationship with TLC member Chilli, which brought much public media of the early 2000s to light. The singer dated several celebrities in the wake of his split.
Other stars he dated include Jennifer Lopez and Keri Hilson, actress and model Naomi Campbell, and stylist Grace Miguel, whom he married in 2015. He and Grace separated in 2018. His relationships would cross over to his music career because most of the inspirations for the songs he would make come from his romantic life, making dating life an important part of his celebrity life.
16) Tyga
Tyga has a history of quite popular relationships, especially in music and entertainment. His most famous relationship recently was with reality television star Kylie Jenner, whom he dated from 2014 until she was 17, which lasted until 2017.
Before dating Jenner, Tyga dated singer Blac Chyna; he fathered a son named King Cairo. This rapper has also dated models, including Demi Rose and Iggy Azalea.
17) Ashton Kutcher
Among Ashton Kutcher's most publicized relationships is his Hollywood glamour romance with his wife, actress Demi Moore. One of the celebrity's first high-profile known publicized marriages marked a union from 2005 to 2013; a difference in age and the resulting publicity by way of publications in the media only underlined this fact.
Before marrying Moore, Kutcher dated his former That '70s Show co-star Mila Kunis, with whom he casually and briefly dated before they made their final commitment to each other in 2015. His on-again-on-again romance with Kunis worked out into forever love, and he is now a dad of two children.
In addition to the contacts listed, Kutcher was also linked to other stars like Brittany Murphy and January Jones, but Kunis was more significant and sturdy for him since they ended up in life within a family.
18) Jared Leto
Jared Leto's performances and artistic persona are eclectic, as is his dating history. One gets the sense of his flair for attraction towards women with status in the entertainment industry. Their names ranged from Cameron Diaz to Scarlett Johansson, even Uma Thurman.
Until now, he has been known to be the boyfriend of actress and model Ashley Olsen for some time, with much talk over his affair with singer-songwriter Lina Morgana, with whom he cooperated pretty often. Recently, he was said to be dating model Valery Kaufman.
19) Chris Evans
Chris Evans has been dating some of Hollywood's big names while enjoying success in the acting world. He was once rumored to be dating actress Jessica Biel in the early 2000s. They finally split up after years of an on-and-off relationship.
Besides Biel, Evans has dated celebrities such as Minka Kelly and Jenny Slate. Recently, he was seen linked with actress Alba Baptista, which has excited fans. Evans' down-to-earth personality has made him a personality with a private life, though charm and good looks have popularized him in the dating world.
20) Mick Jagger
Mick Jagger's love life has received as much attention as the music he makes. One of his most publicized relationships was with supermodel and actress Marianne Faithfull, with whom he arguably became the iconic embodiment. His romances were always in the news, of course, but not necessarily of his choosing and undoubtedly not due to the situation: his very brief affair with Carla Bruni, his extremely short-lived dalliances with the late designer L'Wren Scott, with whom he had a rather serious relationship until her tragic death in 2014.
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