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As Taylor Swift’s young boyfriend, Conor Kennedy, heads back to high school, we look at other stars who have dared to date teenagers.


Taylor Swift and Conor Kennedy
Taylor Swift enjoyed some summer lovin’ over the last few months, proceeding at full throttle into a relationship with 18-year-old Conor Kennedy. They cuddled their way through Cape Cod – and even crashed a Kennedy family wedding. But those summer days and nights are over. On Thursday, as 22-year-old Swift was preparing for her big performance at the MTV Video Music Awards in Hollywood, Conor headed back to high school. Yup, we said high school, not college. Conor, the eldest son of Robert F. Kennedy Jr. and the late Mary Kennedy, was due back at his posh boarding school, Deerfield Academy, in western Massachusetts on September 6. And while his world-famous country singer girlfriend performed a track off her upcoming album, Red, at the VMAs on Thursday night, Conor most likely had to catch her performance on a TV in his single-sex dorm room. Meanwhile, let’s hope Swift likes football because Connor, who plays at Deerfield, has games practically every weekend through early November. Talk about being in different places in their lives! But Swift isn’t the only mega-star who has pursued a relationship with someone who was still treading through his or her teen years.


Miley Cyrus and Justin Gaston
Before Liam Hemsworth was ever a thought in her mind, Miley Cyrus was head-over-heels for another older guy named … Justin Gaston. In 2008, when the “Hannah Montana” star was only 15, she started dating the 20-year-old model. They met through Miley’s dad – Billy Ray hosted “Nashville Star,” the reality show on which Gaston was a contestant. Despite their daughter’s young age, Miley’s parents were both happy about the relationship with Billy Ray calling it “a good thing." No surprise, what Miley and Gaston had wasn’t an everlasting love. In 2009, she announced their split on Twitter, writing, "Why does saying good-bye hurt so much? Life will go on. You will smile again. ... We will smile again." Well, she certainly smiled when new love Hemsworth, 22, popped the question in May 2012. However, “The Last Song” co-stars aren’t rushing down the aisle. “We want to have a long engagement," Miley recently told Marie Claire.


Jerry Seinfeld and Shoshanna Lonstein
Jerry Seinfeld was at the peak of his success while starring in his iconic TV series, “Seinfeld,” and had his pick of ladies – not that there was anything wrong with that. However, the one who caught his eye in Central Park in 1993 was Shoshanna Lonstein – who was just 17 and a senior at the private Nightingale-Bamford School in Manhattan. Seinfeld, who was 38 at the time, and Lonstein embarked on a five-year relationship during which he openly gushed about his young love, calling her "the most wonderful girl in the world” and addressing the age issue by saying, “Shoshanna is a person, not an age. …We just get along. You can hear the click." But not long after she moved to Los Angeles to attend UCLA and explore their relationship, they called it quits. Lonstein, now a fashion designer, later told Details, “I felt like I was losing myself” by dating Seinfeld, who she called a workaholic. “I mean, school's fine, but you need more. And there wasn't much else. So I worked out a lot." Seinfeld went on to marry his current wife, Jessica, in 1998, but that relationship was not without controversy either. They met weeks after Jessica had married someone else. She then quickly filed for divorce and started dating the famed comedian.


Wilmer Valderrama and Lindsay Lohan
Lindsay Lohan’s antics have long been making headlines – even back in 2004. Then 17, Lohan, who had already begun to earn her party girl reputation, started hanging out with “That ‘70s Show” star Wilmer Valderrama. The problem? He was seven years her senior. Although they were often seen together, they didn’t publicly acknowledge their relationship until Lohan turned 18 that July. “We try to keep it more under wraps because it is a lot more meaningful that way," Valderrama said that summer, adding: "We don't need the free press." Once they went public, things didn’t last long. In November, just weeks after Lohan made a cameo appearance on Valderrama's TV series, they called it quits. Lohan's mom, Dina, later called Valderrama her daughter's "first love."


Wilmer Valderrama and Mandy Moore
Valderrama had previous experience with younger ladies. In 2000, Mandy Moore was a fresh-faced 16-year-old who had recently landed a Neutrogena contract and her own show on MTV. She met Valderrama, then 20, soon after at a photo shoot and they started dating. Although their relationship ended in 2002, Valderrama apparently couldn’t keep Moore off his mind. In 2006, he appeared on Howard Stern’s radio show and talked about how he took Moore’s virginity. She later told Elle that his comments were "utterly tacky, not even true, and it hurt my feelings because I like him."


Aaliyah and R Kelly
Looking back, it was no surprise Aaliyah’s 1994 debut album was called Age Ain’t Nothing but a Number. Before she even entered her teen years, she was introduced to hip-hop singer/producer R. Kelly, who took her under his wing. Not only did he become the lead songwriter on her album, which was released when she turned 15, but he also reportedly became her husband after she said “I do” to the then-27-year-old during a secret ceremony. The relationship soon soured and it wasn’t a topic Aaliyah wanted to discuss. When Vibe produced a copy of the marriage license in 1995, she responded, "I'm not married. That's all I really want to say about it." In 2001, Aaliyah died in a plane crash when she was just 22. In the years following her death, Kelly was involved in a legal drama over a video which reportedly showed him having sex with his then-underage goddaughter. Although he was initially charged with child pornography, the "Feelin' on Yo Booty" singer was later acquitted.


Linda Hogan and this 19 year old
After 24 years of marriage, Linda and Hulk Hogan’s 2007 divorce was a nasty one with accusations aplenty. Clearly happy to go their separate ways, Linda’s next move in the romance department was an interesting one. Then 49, she started seeing a 19-year-old who had attended high school with her daughter, Brooke, and son, Nick. Needless to say, her kids weren't thrilled by the news. "I'm totally freaked out," Brooke said at the time. "I personally don't like it at all, or condone." But Linda, who called Hill “an old soul,” moved forward anyway and even became engaged to her younger man in 2010. The relationship wasn’t without problems though – which they hashed out on VH1's “Couples Therapy,” natch – and earlier this year she announced the engagement was off. Too bad … we would have loved to have seen those wedding photos.


Hayden Panettiere and Milo Ventimiglia
Hayden Panettiere found herself in a similar situation to Lindsay Lohan back in 2007. Just 17, she had grown close to her 29-year-old “Heroes” co-star Milo Ventimiglia, who played her uncle on the sci-fi TV series. After repeatedly denying they were involved, they were spotted holding hands in a Los Angeles mall a few months after her 18th birthday. "When you're in the public eye, you try to keep whatever you can private," he later told Details. Their romance fizzled in 2009.


Kobe and Vanessa Bryant
Kobe and Vanessa Bryant have had their ups and downs – they’re back on after she filed for divorce last year – but things started out sweet. In November 1999, the 21-year-old Lakers star was at a recording studio laying down a track on a never-released hip-hop album and met Vanessa, who was 17 and working as a backup dancer in a music video. Although Vanessa was still a senior in high school, they started dating right away and became engaged just six months later. However, that was the end of her in-school high school career. Vanessa received so much attention from classmates about her relationship with the NBA star, she left school and completed her studies independently. Kobe and Vanessa later tied the knot in April 2001 – but with a few key people missing. Kobe’s parents refused to attend the wedding; they were reportedly opposed to the marriage because they felt their son was too young.


Chad Michael Murray and Kenzie Dalton
After a blink-and-you-missed it marriage to his “One Tree Hill” co-star Sophia Bush in 2005 (five months!), Chad Michael Murray, then 24, didn’t run wild as a bachelor or date around. Instead, he immediately embarked on a new relationship – this time with Kenzie Dalton, a 17-year-old extra on his show. Just two months after they became an item, things took a serious turn when, soon after her 18th birthday, he proposed to the high school senior. While they haven’t yet walked down the aisle, they are still happily an item. "She is a little stunner,” Murray recently told Us Weekly. “She is a sweetheart. She is my best friend and we have been together a long time.”


Doug Hutchinson and Courtney Stodden
Did you think we would leave Doug Hutchison and Courtney Stodden off our list? No way. The creep factor is high on this pair because the “Lost” actor was 51 years old when he married the 16-year-old aspiring singer in Las Vegas in 2011. As in ... she needed parental permission in order to say “I do.” At the time Hutchison told E!, "We're aware that our vast age difference is extremely controversial. But we're very much in love and want to get the message out there that true love can be ageless." In August, Stodden – who routinely posts risqué photos of herself, often snapped by her husband, on Twitter – turned 18 and she said she was inundated by offers to do pornography. For the record, she’s not ruling them out, but is hoping to get an offer from Playboy instead.
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