Bruno Pugh
Hollywood is known for its high-profile romances, and certain celebrities seem to have an endless list of romantic partners. We’re exploring the love lives of 15 stars who’ve kept us guessing with their whirlwind romances and high-profile breakups. Get ready for a peek into the world of Hollywood relationships!
Leonardo DiCaprio
Leonardo DiCaprio, the quintessential Hollywood heartthrob, has a storied dating history with 23 girlfriends. His romantic journey began with model Bridget Hall in 1994, and his longest relationship was with supermodel Gisele Bündchen from 2001 to 2005. Over the years, he has also dated high-profile names like Gigi Hadid, Naomi Campbell, and Blake Lively. They married in 2014 and had a daughter, but separated in 2017. Talking of the present times, Scarlett is married to comedian Colin Jost.
Source: ELLE
Kate Hudson
“Relationships are the most challenging things,” Kate Hudson said in the May 2014 issue of SELF. Hudson, the bubbly and charismatic actress, was famously married to musician Chris Robinson from 2000 to 2007, with whom she shares a son. Post-divorce, Hudson dated Owen Wilson, Lance Armstrong, and Matt Bellamy, with whom she has another son. In more recent years, she has been linked to musician Danny Fujikawa, and they welcomed a daughter together in 2018.
Source: People
Kim Kardashian
As high-profile as her career has been, Kim Kardashian’s love life has been no exception. It all began with music producer Damon Thomas in the early 2000s. After a few other relationships, she got married to NBA player Kris Humphries for only a period of 72 days. Her most talked-about romance was with rapper Kanye West, and together they have four kids. Recently, Kim was reportedly linked to Odell Beckham Jr.
Source: Cosmopolitan
Madonna
The Queen of Pop was famously married to actor Sean Penn in the 1980s, a tumultuous relationship that kept the tabloids busy. In the 90s, she dated personal trainer Carlos Leon, with whom she has a daughter called Lourdes. Her marriage to British director Guy Ritchie in the early 2000s resulted in a son, Rocco. More recently, Madonna has been dating her boxer boyfriend, Josh Popper, proving that her love life remains as vibrant as her career.
Source: People
Justin Timberlake
Timberlake has kept fans guessing about his love life for many years. Throughout his career, he has had relationships with celebrities such as Fergie, Britney Spears, Beyonce, Cameron Diaz, and more. However, it was Jessica Biel who captured his heart for good. The couple, known for their chemistry and mutual support, tied the knot in 2012 and have since become Hollywood’s power couple.
Source: AugustMan
Paris Hilton
This heiress-turned-entrepreneur’s romantic life has been a constant source of fascination. Notably, her early romance with actor Leonardo DiCaprio made headlines, followed by her engagement to model Jason Shaw. Moreover, her relationship with Greek shipping heir Stavros Niarchos III (the two split in March 2007) and later engagement to actor Chris Zylka (2017) continued to keep her in the spotlight.
Source: Us Weekly
Drew Barrymore
Barrymore married bartender Jeremy Thomas in 1994 at the age of 19, followed by a brief marriage to comedian Tom Green in 2001. She later dated and had an on-again, off-again relationship with actor Justin Long, known for their chemistry on-screen and off. Later, in 2012, she married art consultant Will Kopelman (divorced in 2016) and had two daughters. Other than these, she also dated Corey Feldman, David Arquette, Jamie Walters, Jermey Thomas, and many more.
Source: ELLE
Britney Spears
One of the most famous headlines of Britney’s dating life has been her romance with Justin Timberlake, which captivated fans with their matching denim outfits. Following their split, Britney’s dating life continued to be a topic of interest, including her marriages to her childhood friend Jason Alexander (annulled after two days) and Kevin Federline (with whom she had two sons). As of now, she is dating her former housekeeper, Paul Soliz.
Source: Us Weekly
Halle Berry
During the late ’80s and early ’90s, as her acting career was on the rise, Hall dated John Ronan, a dentist from Chicago. Her journey then led to marriage with baseball star David Justice on New Year’s Day 1993, though the union ended three years later. Subsequently, she wed singer Eric Benét in 2001, facing challenges stemming from his infidelity before their divorce. Following this, she entered a relationship with French-Canadian model Gabriel Aubry and had a daughter named Nahla. Berry later found love with musician Van Hunt starting in 2020, marking another chapter in her eventful romantic life.
Source: SheKnows
Jennifer Aniston
Beloved for her role in “Friends,” Jennifer had a varied romantic journey in Hollywood. Beginning with actor Charlie Schlatter, whom she met on the set of “Ferris Bueller,” Aniston then dated actor Daniel McDonald for five years. She later dated singer Adam Duritz and actor Tate Donovan before marrying Brad Pitt in 2000, a union that captured public fascination until their separation in 2005. Following her divorce, Aniston had several relationships before marrying actor Justin Theroux, though they parted ways after two and a half years of marriage.
Source: People
Jennifer Lopez
Jennifer Lopez has had a turbulent love life in the public eye. She married Ojani Noa in 1997, divorcing just 11 months later, and then married Cris Judd, which lasted nine months. Lopez gained attention for her relationship with Ben Affleck, beginning in 2002, including an engagement with a notable pink diamond ring, but the marriage never happened. She then dated Marc Anthony from 2004 to 2011 and has been linked romantically with Drake and Alex Rodriguez. Reuniting with Affleck in 2021, they finally married after reigniting their engagement.
Source: People
Rihanna
Rihanna’s dating life has been a subject of public interest over the years. She dated Chris Brown from 2007 to 2009 before their relationship ended amid a highly publicized domestic violence incident. Following this, Rihanna dated Drake (2009 to 2016) and Hassan Jameel, a Saudi businessman with whom she dated from 2017 to 2020. In 2022, she welcomed her first child with her longtime friend turned lover, A$AP Rocky.
Source: People
Taylor Swift
The iconic singer has often been criticized for her relationships, which have inspired some of her biggest hits. At just 18, she dated Joe Jonas, a relationship that ended abruptly over a 25-second phone call. In 2009, she briefly dated Lucas Till before setting on whirlwind romances with musicians like John Mayer and actors like Jake Gyllenhaal. Her dating life continued to captivate the public as she moved on to brief relationships with Connor Kennedy and Harry Styles. Since May 2017, Taylor has maintained a more private relationship with actor Joe Alwyn, which lasted until 2023.
Source: Cosmopolitan
John Mayer
Mayer’s dating history is a star-studded affair, beginning with actress Jennifer Love Hewitt in 2002. He then moved on to Jessica Simpson in 2006, right after her divorce from Nick Lachey, and had a brief fling with Cameron Diaz the same year. Mayer’s list of exes also includes Minka Kelly, Jennifer Aniston, Taylor Swift, and Kim Kardashian. Recently, there were rumors that he was dating Andy Cohen, but nothing was ever confirmed.
Source: PopSugar
Scarlett Johansson
Starting her romantic journey in NYC, Scarlett dated Jack Antonoff during their time at the Professional Children’s School. In 2004, she briefly dated Jared Leto before entering a serious relationship with Josh Hartnett until 2007. She then dated and married Ryan Reynolds, tying the knot in 2008 but splitting in 2010. After a brief romance with Sean Penn, Scarlett found love with French journalist Romain Dauriac in 2012. They married in 2014 and had a daughter, but separated in 2017. Talking of the present times, Scarlett is married to comedian Colin Jost.
Source: PopSugar
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