Celebrity Relationships That Made Their Families Uncomfortable

Here's to love and awkward family dinners!

Getting the family on board with your significant other isn’t always easy and it’s almost never fun.

Are you in love with your ex’s adopted daughter? Do you have plans to marry the parent of your younger sibling’s children? Are you dating your half-sister’s boyfriend’s baby mama? If you’ve answered yes to any of the previous questions, you might be subject to: uncomfortable family drama.

The following celebrities had romantic relationships that gave their families headaches for a variety of reasons. Though some of these couples ended up calling it quits, many are still together (or at least on good terms). That just goes to show that sometimes, how you feel about your S.O. matters more than your family members’ opinions.

Here’s to love and awkward family dinners, am I right?

  • 1 Rob Kardashian and Blac Chyna
    Rob Kardashian and Blac Chyna’s whirlwind romance is rumored to be cause of tension in the Kardashian-Jenner family. A source told People that Rob’s family “is really not into the engagement.” Perhaps this is due to the fact that Blac Chyna is the baby mama of Rob’s sister Kylie’s boyfriend, Tyga. Or maybe not.

  • 2 Woody Allen and Soon-Yi Previn
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    Woody Allen fell in love with his ex Mia Farrow’s adopted daughter, Soon-Yi Previn. Mia reportedly found out about the relationship in 1992, after seeing nude Polaroids of Soon-Yi, who was “either 18 or 20” at the time, on Woody’s mantle. Woody and Soon-Yi eventually married and now have two kids together.

  • 3 Jermaine Jackson and Alejandra Oaziaza
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    Here’s a jam-packed sentence: Michael Jackson’s older brother Jermaine married the mother of younger brother Randy’s children, Alejandra Oaziaza. Randy and Alejandra had two children at the time that she and Jermaine started seeing each other. Jermaine moved into her and Randy’s house while Randy was away, and in 1995, Jermaine and Alejandra secretly married. They went on to have three children of their own.

  • 4 Selena Gomez and Justin Bieber
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    Selena Gomez’s family apparently wasn’t feeling her reunion with Justin Bieber in 2014. Gomez’s fam pegged Biebs for “a punk” and dubbed him “the worst thing to ever happen to Selena,” according to PopCrush.

  • 5 Howard and Beth Stern
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    Howard Stern’s wife Beth told Huffington Post that her mother didn’t take the initial news of her dating Howard lightly. Beth said that her mom, a “devout Catholic,” hung up on her, didn’t talk to her for two weeks and “rushed to church” upon hearing that her daughter wanted to marry Howard.

  • 6 Miley Cyrus and Patrick Schwarzenegger
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    Maria Shriver was supposedly unhappy about her son Patrick Schwarzenegger’s romantic relationship with Miley Cyrus. Back in December 2014, Hollywood Life reported that Patrick had uninvited Miley from his family’s Thanksgiving celebrations after his mom ultimately banned Miley from coming.

  • 7 Chris Brown and Rihanna
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    Clinton Brown, Chris Brown’s father, “really didn’t want him and Rihanna back together,” according to a 2013 interview he gave to the NY Daily News. “You have to have a balance in a relationship. You have to have someone who is spontaneous and whimsical but you also have to have someone who is grounded and logical,” he said, adding that he liked dating prospects Karrueche Tran and Jordin Sparks for his son.

  • 8 Katy Perry and John Mayer
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    Katy Perry’s parents supposedly didn’t approve of her dating notorious bad boy John Mayer. CelebsNow reported in 2012 that “sources” said Katy’s parents had a “strong dislike” for John, finding his attitude towards women “reprehensible.” Katy’s parents also apparently had someone else in mind for her to date. “They’d love Katy to go out with someone nice like Robert Pattinson,” a source said.

  • 9 Leonardo DiCaprio and Blake Lively
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    Leonardo DiCaprio’s mom Irmelin apparently did not take kindly to former girlfriend Blake Lively. Blake “wouldn’t shut up about herself” while meeting Leo’s mom and talked about Gossip Girl and modeling for Chanel, according to Perez Hilton. “Because she seemed so into herself, Irmelin couldn’t stand the girl,” the site reports.

  • 10 Ashlee Simpson and Evan Ross
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    Music legend Diana Ross apparently didn’t want her son Evan to end up with Ashlee Simpson. A source told The National Enquirer in 2013 that “Diana told Evan she likes Ashlee well enough, just not for him and definitely not as a future daughter-in-law.” Another source said, “Plain and simple, Diana doesn’t ap­prove of Ashlee because of her screwy family and wild-child reputation.” Ashlee and Evan got married in 2014.

1/2 Cartoon, 1/2 Beyhive.