High school dating is a precarious experience even for the most well-adjusted teenager. Halfway between childhood and adulthood, high school teens have to deal with all the usual peer pressure mixed in with raging hormones, rapidly changing bodies, a growing brain, and growing responsibilities.
Looking back at Hollywood high-school sweethearts provides a precious glimpse at what celebrities were like before they were famous – or, in some cases, what’s it’s like to date in high school as a famous teenage celebrity. There’s also the inherent thrill of learning about boyfriends and girlfriends who dated these celebrities before their exes became the huge stars they are today.
There are ex-boyfriends who have cheated on women who turned into superstars, in some cases inspiring the art that propelled them to fame. There are other Hollywood high school dating stories that raise eyebrows, and provoke uncomfortable questions about exactly what happened.
Not all high school sweethearts ended their relationships in tragedy, controversy or disaster. Some of the high school couples on this list serve as reminders that teenagers can be as kind and chivalrous as they can be unpredictable, creating positive memories of growing up that last a lifetime. Some of these celebs even remain in contact with their non-celebrity past loves today.
10. Emma Watson – Tom Ducker
Emma Watson‘s first significant romance was rugby player Tom Ducker, who she dated as a teenager while working on the Harry Potter series of films. Paparazzi spotted the two enjoying their time together on the French Riviera, dining on lobster and sipping fine champagne.
She reportedly broke up with him after pictures surfaced of Tom partying with other girls. A source close to Emma stated that the star was understandably upset, considering him her first love.
The actress has since moved on to further success after the Harry Potter franchise, choosing dating partners who seem to treat her with more respect than the rugger player Tom.
9. Ben Affleck – Cheyenne Rothman
According to People magazine, Ben and Cheyenne met at a summer camp while they were teens. The two remained an on-and-off couple for seven years as Affleck bounced from the University of Vermont to Hollywood, after being rejected by Harvard.
Affleck went on to be declared the sexiest man alive in 2002, and won Oscars for Good Will Hunting and Argo while going through a string of high profile relationships before settling down and building a family with Daredevil co star Jennifer Garner.
8. Taylor Swift – Sam Armstrong
Taylor Swift‘s history of drawing inspiration for her songs from her dating life may have started in high school, when she dated Sam Armstrong. Their relationship came to a halt when she discovered that Sam was cheating on her.
This betrayal caused Taylor to write “Should’ve Said No”, which features lyrics directed at Sam that sing, “you should’ve thought twice before you let it all go.”
During her wildly successful career, Swift has made a living writing about the good, the bad and the ugly side of dating, including songs about Taylor Lautner, John Mayer, Jake Gyllenhaal and Harry Styles. So far, works inspired by these heartbreaks have earned Swift a legion of devoted fans and seven Grammys.
7. Brad Pitt – Kim Bell
Kim Bell dated Brad Pitt back in the 1970s while growing up in Springfield, Missouri. She remembers him as “a good first boyfriend” because of how well he behaved with her. Of course, they went their separate ways in the 9th grade, both of them moving on to raising their own families.
In a recent interview, Bell recounted Pitt’s charm and personality as a young teen, going to parties and events together, stating that the entire town knew that Brad had a bright future.
Recently, Kim challenged Brad Pitt to take part in the ALS Ice Bucket Challenge, revealing that her husband, Howard Bell, passed away because from the illness.
6. Kim Kardashian – TJ Jackson
After causing a stir on Oprah by describing her use of birth control at 14, there was rampant speculation about Kim K’s teenage dating life. This led to the revelation that her first high-school sweetheart was TJ Jackson, nephew of Michael Jackson.
This leak is attributed to Pam Behan, the nanny of the Kardashians between 1991 and 1996. The former nanny revealed this to the world as part of a publicity campaign for the her book of memoirs about her time with the family.
Since then, Kim has gone through failed marriages with Damon Thomas and Kris Humphries before finding marital bliss with Kanye West, rising to the status of celebrity through her roles on reality television and plenty of clever publicity stunts.
5. James Franco – ‘Jasmine’
James Franco admits he was very shy at high school, stating that during his early teen years he was “a little confused and mixed-up when it came to dating.” He considers himself lucky that he dated his high-school girlfriend – only ever mentioned in interviews by her first name, Jasmine – during his last two years of secondary school.
Apparently, Franco caught the acting bug out of jealousy. When Jasmine decided to act in a high school play, he decided to audition because he didn’t want another actor kissing his girlfriend. In addition to stolen kisses, he also claims he was jealous of the fact that another guy was doing what he wanted to do: write, direct and act in plays.
4. Scarlett Johansson – Jack Antonoff
ScarJo and Jack met when they were teenagers enrolled in the Professional Children’s School in New York , dating for about a year. When Dunham saw the old photos of her boyfriend’s high profile high school sweetheart, she said she thought she “was hallucinating.”
Scarlett is one of the biggest Hollywood stars on the planet while Lena is behind the Emmy and Golden Globe winning TV series Girls, making Jack Antonoff a potential male muse.
3. Johnny Depp – Lori Allison
Johnny Depp dropped out of high school to pursue a career in music before switching to acting, but he still fell in love young. In fact, he was married by age 20 – a tidbit that’s not frequently mentioned in relation to Depp’s many high profile relationships.
He met Lori Allison, 5 years his senior, in Miami. She was a makeup artist, he was the new guy in L.A. trying to make it big with his band. The marriage only lasted 2 years, but it was through Lori that he first met Nicolas Cage. This important connection would land him is first major cinematic role in Nightmare on Elm Street.
2. Justin Timberlake – Fergie
It’s a little-known fact that when he was only 16, Justin Timberlake was dating 23 year old Stacy Ferguson, better known by her current stage name Fergie. At the time, she was part of the group Wild Orchid, while he was ascending to pop superstardom.
Fergie says she was with Justin before he became serious with Britney Spears, another one of his famous high-school loves.
Justin went on to become one of the most popular and best selling artists, successfully selling millions of albums as part of NSYNC and through his solo act, eventually acting in Oscar award winning features such as The Social Network.
1. Beyoncé – Lyndall Locke
Beyoncé and her high school boyfriend Lyndall Locke dated for nine years, meeting for the first time at a youth church event.
He has admitted that he cheated on Beyoncé five times while they were together. He made the admission after Beyoncé was wooed by Jay Z when she split with Locke – a considerable upgrade for Bey.
“Who cheats on a woman as beautiful as Beyoncé?”, Lyndall lamented. “Well, I am that man and it’s something that’ll always haunt me.”
Of course, Beyoncé has become one of the most successful and powerful figures in show business while Lyndall reminisces to celebrity blogs about his infidelities.
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