Top 10 Worst Celebrity Boyfriends

We’re sure a lot of you out there asked yourselves: What is Britney thinking? Well, the whole world watched and wondered as the pop princess had a very public meltdown in 2007. Behind the scenes, however, she was in the midst of a bitter divorce from then-husband Kevin Federline, during which K-Fed used Britney’s image issues against her to get sole custody of their two children. However, the backup dancer wasn’t exactly a model of good behavior: the father of six has children with three different women and even ditched his pregnant girlfriend for Britney. So, don’t shed any tears for K-Fed: he reportedly gets $20,000 in child support every month.

Hell hath no fury like a Kanye scorned. Though he’s one of the most successful rappers of his time, Kanye’s public image has largely been defined by his epic rants and feuds. Case in point: Amber Rose. Kanye kicked off 2016 with an epic tweet storm aimed at Wiz Khalifa and their mutual ex, Amber Rose. Yeezy dished out over 25 tweets, and even took things to the real world, stating in a radio interview that he had to take “30 showers” after dating the ex-stripper. But in the end, Rose got the last laugh. It’s safe to say Kanye and Kim K won’t be having Amber over for any dinner parties.

From a legendary film career to a stint in public office, everyone’s favorite strongman seems to have it all. However, there’s no denying Arnold Schwarzenegger’s checkered past with women. Arnold’s behavior made headlines when multiple women came forward with claims of sexual misconduct while he was married to Maria Shriver. Still, Shriver stood by her man, and all seemed well throughout Arnold’s tenure as the governor of California. That is, until 2011 when the couple announced their split after 25 years, followed by the bombshell revelation that Arnold had a love child with former nanny Milfred Baena. We’re guessing Maria won’t be uttering Arnold’s famous catchphrase anytime soon.

#7: John Mayer

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“Don’t kiss and tell” is a cardinal rule of dating, but John Mayer didn’t seem the memo. The “Your Body Is a Wonderland” singer is revered for his soft-rock anthems and has been linked to many a Hollywood bombshell. But his comments about them to the media have left many fans scratching their heads. John famously referred to ex Jessica Simpson as “sexual napalm” and as addictive as “crack cocaine” during a 2010 Playboy interview. He also held a spur-of-the-moment press conference after splitting with Jennifer Aniston – because, why not? John finally got a taste of his own medicine when his exploits were documented in Taylor Swift’s hit “Dear John.” Dear John: please, stop talking.

Cheaters never prosper… unless, of course, you’re Dean McDermott. After embarking on an affair with her while he was still with his first wife, this reality star married into Hollywood royalty when he wed heiress Tori Spelling in 2006. The couple went on to have five children and what appeared to be marital bliss. It hit the fan in 2013, however, when Dean admitted to cheating. The following year, the Canadian reality star went into rehab for what he cited as “health and personal issues.” Tori forgave him and the couple remains together; however, Dean’s infidelity was documented in the first season of the reality series, “True Tori,” immortalizing his sexploits for years to come.

Not many women can resist the allure of a charming Brit. So it came as no surprise when Sienna Miller began dating her “Alfie” costar Jude Law in 2003. Though the couple went on to get engaged, Jude’s behavior ensured the two wouldn’t live happily ever after. In 2005, Jude’s former nanny gave a detailed account of her affair with the actor. He went on to publicly apologize for his actions, but his squeaky clean image was never restored. The couple did try to work it out, but Sienna eventually allegedly cheated on Jude with 007 himself, Daniel Craig – proving that what goes around, comes around.

Let’s hope Bieber fever isn’t easily contracted. Justin Bieber is one of the world’s biggest pop stars, but his behavior behind the scenes has led many to question if he’s worthy of the adoration of his on-again, off-again girlfriend Selena Gomez. Justin’s many extracurricular activities include being caught coming out of a Brazilian brothel, vandalizing a neighbor’s home and getting busted for a DUI. Things escalated when Justin got in a fight with Orlando Bloom after making disparaging remarks about his Bloom’s ex-wife Miranda Kerr, claiming she had said that she’d “make a man” out of the young singer. Yes, Justin, it’s probably too late to say sorry.

Breakups are hard, but they’re even harder when they happen via text message. That’s something Katy Perry knows firsthand thanks to her ex-husband, Russell Brand. This British comedian wooed the pop star and the two eventually married in India in 2010. Their nuptials were short-lived, however, and the two broke up in 2011 after just over a year of marriage. Perry later revealed that Brand pulled the ultimate brutal breakup move by ending things via text on New Year’s Eve 2011. A few years later, Brand dug himself a deeper hole in his biographical documentary “Brand: A Second Coming,” where he referred to Perry’s world as “vapid, vacuous, and plastic.” Ouch.

What do you do when you’re one of the world’s richest athletes? If you’re Tiger Woods, the answer is cheat… a lot. The legendary golf champion had quite the fall from grace after rumors surfaced that he had cheated on his wife, Elin Nordegren. Speculation ran rampant when, in 2009, Tiger mysteriously crashed his SUV outside his Florida home. Yada yada yada, turns out, the rumors were well founded: over a dozen women came forward revealing their affairs with the golfer. Tiger fessed up to his “transgressions” in a very public press conference, was later reportedly treated for sex addiction and officially divorced his wife in 2010. Meanwhile, the whole world is still waiting for his comeback.

Don’t mess with America’s Sweetheart. Jesse James learned that lesson the hard way when he cheated on beloved actress Sandra Bullock. The reality star married the future Oscar winner in 2005. By 2010, however, James found himself embroiled in a mega scandal, with several women alleging affairs. James quickly apologized, but it wasn’t enough and his divorce from Bullock was finalized. The worst part? He didn’t learn from his mistake. He moved on with famed tattoo artist Kat von D, and the couple even got engaged. But she alleged that James cheated on her with no less than 19 women. Coincidently, that’s probably the number of fans he has left after showing his true colors to the world.