By Mark Gray
5:14pm PDT, Aug 3, 2023
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Exes are like opinions — we've all got 'em! And in Britney Spears' case, there are plenty! These days, she's married to actor and fitness model Sam Asghari, but sometimes we can't help but wonder what happened to the men from her past… including this one, who was arrested (again!) in August 2023…
It was one of the most infamous marriages in entertainment history: In the early morning hours of Jan. 3, 2004, Britney Spears married childhood friend Jason Alexander in Las Vegas. After a night on the town, they exchanged vows at the Little White Wedding Chapel. She wore a white baseball cap, ripped jeans and a crop top. But 55 hours later, she had the marriage annulled.
Keep reading to find out what happened to him and more Britney exes…
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In the years following their annulled marriage, Jason Alexander did several media interviews indicating that he was in love with Britney Spears. In 2015, Jason — seen here at a #FreeBritney rally in Los Angeles in 2020 — was jailed in San Francisco for nearly four months for allegedly beating a girlfriend so badly that she needed crutches. He initially pleaded not guilty to all charges but ultimately pleaded guilty to a domestic violence offense.
After his release, he was put on probation for three years, which he finished in 2018. In January 2022, he pleaded guilty to stalking an unidentified woman in Tennessee and was sentenced to 11 months and 29 days of probation for violating an order of protection and aggravated stalking. On June 9, 2022 — Britney and Sam Asghari's wedding day — Jason showed up at their home and streamed live on Instagram as he attempted to crash their wedding. He was eventually restrained and arrested by officers from the Ventura Sheriff's Department and booked for trespassing, vandalism and two batteries related to his physical altercations with Britney's security, TMZ reported. He pleaded no contest to the two misdemeanor counts and was sentenced to time served (he spent 64 days in jail, according to court records obtained by NBC).
In March 2023, Britney's ex remarried: A month after his nuptials, Page Six obtained public records confirming he'd wed a woman named Rebecca Bell — though he was still posting about ex-wife Britney.
In August 2023, Jason was arrested on stalking charges and held in a Tennessee jail with a bond set at $50,000, TMZ reported.
MORE: Jason Alexander's booking photo and more celebrity mug shots
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Britney's first high-profile romance was with a fella named Justin Timberlake. The couple dated from 1999 to 2002. They were basically the homecoming king and queen of entertainment, delighting fans with their young love and matching award show outfits (like these iconic and unfortunate looks they wore to the 2001 American Music Awards). The onetime "The All New Mickey Mouse Club" co-stars split amid rumors that Britney cheated on Justin, something he has implied in his hit song "Cry Me a River."
MORE: Britney Spears' best fashion of all time
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These days, Justin Timberlake is one of the biggest stars in the world, having sold tens of millions of albums globally as a solo artist (he's sold more if you include his time in *NSYNC). He's won 10 Grammys, four Emmys and a slew of other awards. In 2012, he married actress Jessica Biel; they've since welcomed two sons.
MORE: Notorious celebrity cheating scandals
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Choreographer Wade Robson is sort of a legend in Britney Spears folklore — many media outlets alleged that she cheated on Justin Timberlake with Wade, something Justin implied in "Cry Me a River." Regardless of that tabloid fodder, Britney and Wade were linked for several months in 2001 and 2002.
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Wade Robson continued his involvement in the dance world. In 2007, he joined "So You Think You Can Dance" as both a judge and choreographer. He's also gone on to choreograph animated films, stage shows and even world tours. In 2013, he claimed that Michael Jackson sexually assaulted him when he was young, but his lawsuit was dismissed. He detailed his allegations in the 2019 documentary "Finding Neverland." Wade — who in recent years has hosted a podcast and continued to teach dance while also working as a life coach — found love with Amanda Rodriguez, a creative directing partner on "So You Think You Can Dance." They have a child together and live in Hawaii.
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Did you forget about this one? Back in 2003, Britney Spears and Colin Farrell briefly dated — they even appeared on the red carpet at the premiere of "The Recruit" together. Both remained coy about the romance, at one point claiming they were just friends. But ultimately, Britney admitted there was some spit swapping. "Yes, I kissed him," she told W magazine. "He's the cutest, hottest thing in the world — wooh! … But it was nothing serious."
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Since his fling with Britney Spears, Colin Farrell has won two Golden Globes (in 2009 and 2023), been nominated for an Oscar (in 2023) and starred in a cache of blockbusters including "Horrible Bosses," "Total Recall," "Fantastic Beasts and Where to Find Them" and "The Batman." He's had his issues, though, and checked into rehab in 2005. In 2017, he told talk show host Ellen DeGeneres he was 10 years sober. Like Britney, Colin has two sons — James (with model ex Kim Bordenave) and Henry (with actress ex Alicja Bachleda). Colin has been a huge advocate for children with special needs as James has Angelman syndrome, a rare neuro-genetic disorder that causes developmental disabilities and neurological problems.
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Huh?! That's how many people felt when Britney Spears began dating backup dancer Kevin Federline in 2004 (especially since actress Shar Jackson was pregnant with his second child at the time). Within three months, they'd gotten engaged, and they married in September 2004. Kevin and Britney had two sons together — Sean Preston, born in 2005, and Jayden James, born in 2006. Nearly two months after their youngest son's arrival, Britney filed for divorce, reportedly catching Kevin totally off guard. A day after the filing, he asked for physical and legal custody of their children. Their divorce was finalized in July 2007.
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Kevin Federline was awarded physical custody of his and Britney Spears' children in October 2007 amid her much-publicized mental health crisis. He attempted to launch a music career, started DJing and released a song called "Goat" in February 2018. He's also appeared on several reality TV shows including VH1's "Celebrity Fit Club: Boot Camp" in 2010 after he gained a significant amount of weight in the wake of his divorce from Britney.
Kevin married Victoria Prince in Las Vegas in 2013. They welcomed daughters in 2011 and 2014 (K-Fed has six kids in total). In 2018, Kevin — who for a decade had been getting $20,000 a month in child support from Britney — fought her for more money and won in an out-of-court settlement that saw her forking over several thousand more each month for their sons. Britney was also ordered to pay K-Fed $110,000 for his lawyer fees. She was "very unhappy" with the outcome, E! News reported.
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Criss Angel was one of the many men Britney reportedly dated in 2007 (others to whom she was linked that year include producer J.R. Rotem, model Isaac Cohen and singer Howie Day). Criss was initially hired by Britney to help her with her 2007 MTV Video Music Awards performance, which was an utter disaster. Criss maintained that the two never dated, despite the many photos of them together.
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Following his reported romance with Britney Spears, Criss Angel had a high-profile relationship with Playboy model-turned-reality TV star Holly Madison. In 2008, Criss began what would be a 10-year magic show in Las Vegas at the Luxor. The highly skilled magician and illusionist was awarded a lifetime achievement award from the International Brotherhood of Magicians in 2018. The same year, he launched a new show at Planet Hollywood. His personal life often made headlines as well. In 2014, Criss and his girlfriend, Shaunyl Benson, welcomed son Johnny Crisstopher, who was diagnosed with acute lymphoblastic leukemia in 2015. At the time, Criss and Shaunyl had just separated and Johnny had just relocated to Australia. The pair reconciled welcome a second son in 2019 and a daughter in 2021. In 2022, Criss announced that after years of ups and downs, Johnny's cancer was in remission.
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Britney Spears e dated paparazzo Adnan Ghalib for a year in 2007 and 2008. Many in the singer's inner circle were disappointed when her fling with Adnan began since they thought he was using her for fame and to further his career. They reportedly split over the telephone. Britney also filed a restraining order against him, which kept him from away from her for three years.
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No surprise here, but Adnan Ghalib's profile took a huge hit after he dated Britney Spears. In 2012, he testified in a trial involving Britney's former manager, Sam Lutfi, and her family. In 2018, he did an interview with The Sun in which he claimed he was essentially Britney's confidante and took credit for repairing her fractured relationship with her dad, Jamie Spears, who ruled her life under a conservatorship she succeeded in ending in 2021. Adnan (seen here in 2009) moved to Seal Beach, California, where he works as a security consultant.
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Britney Spears' first serious post-divorce romance came with her agent, Jason Trawick, whom she began dating in the summer of 2009. They got engaged in Las Vegas in 2011. Britney's family was so sure of him that Jason was even named a co-conservator of the pop star's personal affairs alongside her dad at one point. However, in 2013, Jason and Britney split, ending their engagement. In doing so, he resigned from his position as co-conservator. "Britney wants to grow her family," a source told People magazine at the time. "Jason loves her boys but he is not in a place to have his own." Jason later shared his take on why they split…
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In 2013 following his split from Britney Spears, former talent agent Jason Trawick was romantically linked to "Hunger Games" actress Leven Rambin. In 2016, he executive produced the crime movie "Marauders" starring Bruce Willis. Jason — seen here in 2017 goofing around with a valet outside a Los Angeles hotspot — went on to bet big on the alcohol industry when he became a partner at Minute Mixology, a company that makes ready-made cocktails and single-serve cocktail mixers. He now lives in Las Vegas.
In January 2023, he resurfaced on actor Kevin Connolly's podcast where he shared his thoughts on Britney's conservatorship, which ended in 2021, and their breakup. "Listen, did she need a conservatorship when I was there? Yes. I'll be the first to say it. I think she needed some guidance," as well as someone to oversee her finances because "she doesn't understand what things cost," Jason said, adding that it was also necessary because she needed "therapy" and to be stopped "from seeing certain individuals that were not great [influences]." Jason said he believe Britney's father, Jamie Spears, "100%" only wanted to help her, "unless they can prove he somehow stole money from her." He further said he's happy his ex got "the opportunity to show the world" that she can lead her own life after she got the conservatorship dissolved in 2021. "If she fails, then she fails," he said, but "I want her to prove [naysayers] wrong."
Jason also explained why he and Britney ended their engagement. According to him, Britney, not Jamie, was the one who "asked me to be [co-]conservator" over her person, but the role "took a toll" on his relationship with Britney. "At the end, it was just … a lot of fighting. It wasn't fair in front of the kids," Jason said of the singer's boys with ex-husband Kevin Federline. Their breakup "wasn't easy. It wasn't one of those breakups where … you still saw each other. It was a final," Jason said, and "the hardest part was the kids. I'd known them since Preston was born and Jayden was basically a newborn. That was really hard on me — not seeing them … They were 7 and 8 when I left."
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David Lucado began dating Britney Spears in February 2013. The two met at a party and she called him her "love" during an appearance on "The Ellen DeGeneres Show." But in the summer of 2014, the two split after pictures of David kissing another woman surfaced. "Well, by now everyone knows my boyfriend cheated on me," Britney told a crowd on stage at a Las Vegas concert.
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According to his LinkedIn page, David Lucado (seen here in 2014) is a legal investigator for Rapid Sign Now, a legal services company in Southern California. He's been with them since 2009.
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In late 2014, Britney Spears struck up a new romance with writer-producer Charlie Ebersol. The son of legendary NBC Sports chief Dick Ebersol and actress Susan Saint James, Charlie was often spotted at Britney's Las Vegas residency show. The two didn't hide their romance, taking it public at the Billboard Music Awards in 2015. Earlier in the relationship, "everyone thought he might end up asking her to marry him," a source told People magazine. "It just faded away, and they moved apart." The couple split in June 2015 after eight months of dating.
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Charlie Ebersol still has a pretty high profile. In 2017, he directed a documentary for ESPN, "This Was the XFL," as part of its 30 for 30 series, and married StyleSeat CEO Melody McCloskey in Tennessee; they've since welcomed two kids. In 2018, Charlie and a former NFL executive created a new professional football league, the Alliance of American Football, that kicked off games in 2019 but only lasted for eight weeks of play before filing for bankruptcy. He was also a co-producer on the CNBC show "The Profit," which ended in 2021 after eight seasons. In 2022, a show he executive produced, "The Recruit" starring Noah Centineo, was a hit for Netflix.
