10 Celebrity Exes Whose Shady Breakup Drama Gives Me Life

Pete Davidson and Ariana Grande’s relationship burned bright and fast. And after they broke off their 5-month engagement in 2018, there was understandably some fallout — especially after Grande’s 2019 interview with Vogue. In it, she called her relationship with Davidson “an amazing distraction.” She added, “It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.”

Her song, “thank u, next,” also referenced her relationship with Davidson. “Even almost got married / And for Pete, I'm so thankful,” the lyrics read — so not shady, but that didn’t exactly curb Davidson’s anger over her comments on the relationship.

Davidson hit back during his 2020 Netflix special Alive From New York. “Can you imagine if I did that? My career would be over tomorrow if I spray-painted myself brown and hopped on the cover of Vogue magazine and just started sh*tting on my ex,” he joked. “Can you imagine if I did that sh*t? If I was just like, ‘Yeah, I was just f*cking her 'cause I was bored, and then Fortnite came out.’ It would be insane.” Safe to say, they aren’t exactly friendly exes — at least, not yet.

Miley Cyrus hasn’t shied away from shading her ex-husband, Liam Hemsworth. In Dec. 2020, when Cyrus was tagged in a TikTok claiming “If Miley comments, we’ll get married,” she left a cheeky reply. “Hope it goes better for you two than it did for me,” she wrote. “Congrats.” 👀

That wasn’t the only time Cyrus veered into petty territory when it comes to talking about Hemsworth, whom she married in Dec. 2018 and divorced in Aug. 2019. That same month, Cyrus opened up about their divorce during an interview with Howard Stern. In it, Cyrus cited “too much conflict” as one of the reasons they decided to part ways. She explained, “When I come home, I want to be anchored by someone... I don't get off on drama or fighting.”

Hemsworth has kept a low profile since the divorce with the exception of one IG statement. “This is a private matter and I have not made, nor will I be making, any comments to any journalists or media outlets. Any reported quotes attributed to me are false,” he posted on Aug. 12, 2019.

Kanye West and Amber Rose were together for two years, from 2008 to 2010. But the fallout from that relationship lasted much longer. In 2015, West insulted Rose, by insinuating that he “had to take 30 showers before [he] got with Kim,” per Entertainment Tonight.

In Oct. 2021, Rose explained her current feelings toward her ex . “I don’t want my life to be like that. I’m not that type of person. And I don’t know if he says things to make his wife more comfortable, but to slut-shame me and say you needed 30 showers, like, bro, you took me around the world. Since when do you need 30 showers?” she explained during an interview on the No Jumper podcast. “He has picked on me for 10 years. He has bullied me for 10 years.”

Demi Lovato called off their engagement to Max Ehrich in Sept. 2020 after fans uncovered some questionable tweets from the the actor. In one from 2018, Ehrich wrote, “I'm going to marry Selena Gomez.” (Not exactly a great look when you’re engaged to someone who is not, in fact, Selena Gomez. Plus, considering Lovato and Gomez used to be besties, this did not sit well with anyone.)

Around one week later, Demi called off the engagement. “It was a tough decision, but Demi and Max have decided to go their separate ways to focus on their respective careers. They have respect and love for one another and will always cherish the time they spent together,” a source reportedly told People.

Ehrich then hit back with a surprising accusation in his IG Stories. “Imagine finding out the status of your relationship through a tabloid ... while your [sic] in the middle of filming a biopic movie about a Pastor in a Christian Church whose intention of the film is to help people,” he wrote. However, Demi’s rep denied that version of the story.

It’s no secret that Taylor Swift likes writing about her personal experiences, including her failed relationships. No, not all of her songs are about her exes — can we please end that narrative here and now? — but a fair few of them allude to her romantic past. The best example of this? My personal fave is “Dear John” off of her 2010 Speak Now album.

Though Swift has never officially confirmed that it’s about her ex John Mayer, Swifties are convinced. In the song, Swift sings, “Dear John, I see it all, now it was wrong / Don't you think 19 is too young / To be played by your dark twisted games, when I loved you so?” The timeline definitely matches up: When this duo dated from Dec. 2009 to Feb. 2010, Swift was 19 and Mayer was 32.

Mayer also hasn’t been too reluctant to shade Swift. In 2012, he told Rolling Stone that Swift’s song “really humiliated him” and called it an example of “cheap songwriting.” Plus, per Seventeen, in 2016, he tweeted and later deleted, “Tuesday, December 13 may be the lamest day of the year, conceptually.” Dec. 13 is Swift’s birthday. Not to mention, on an IG Live in 2019, Mayer mocked Swift’s “Lover” lyrics.

Bella Thorne and Tana Mongeau dated for one year before splitting up in Feb. 2019. Although they initially ended on good terms (Thorne even posted a sweet IG for Mongeau’s birthday in June), it didn’t stay that way for long.

By July 2019, Thorne had officially put an end to their run as friendly exes. She tweeted, “Tana and I are no longer good. She broke girl code I’m over it,” but didn’t provide any more details. Mongeau replied, “????? imagine taking every time ur mad at me to twitter but then telling ppl how much u care about me.................... wtf is this b :/.”

Believe it or not, things got more complicated from there. Thorne shot back, “U legit started dating me for twitter. How about u answer ur phone and talk to me instead of being on Twitter.” Mongeau countered, “Dude what are you doing bella? Like I have no idea why you’re mad, I've been texting you every minute since you tweeted, and for you to be tweeting me something as hurtful as saying I dated you for Twitter is literally f*cking nuts & if you honestly think that d*mn i lost you.” Yikes.

Back in 1999, no couple was hotter —or seemed more in love — than Britney Spears and Justin Timberlake. But, when the duo split in March 2002, the post-breakup drama was... rough. JT featured a Spears lookalike in his 2002 “Cry Me A River” music video, where he pinned the blame of their breakup firmly on her and included vague cheating accusations. With lyrics like “You don't have to say, what you did / I already know, I found out from him” and “It wasn't like you only talked to him / And you know it,” he didn’t keep things subtle.

Timberlake’s post-breakup interviews were just as bad. Per Insider, when one radio host asked him whether or not he “f*ck[ed] Britney Spears” — a loaded question considering Spears had openly talked about wanting to wait for marriage to have sex — Timberlake laughed and replied, “OK, I did it.” (Gross.) In a 2003 interview with Diane Sawyer, Spears admitted she felt “exploited” by Timberlake’s comment on their sex life.

It wasn’t until 2021 — after the Framing Britney Spears documentary featured these moments — that JT formally apologized on Instagram for the times he “fell short” during his interactions with Spears.

Selena Gomez and Justin Bieber were a couple of teen heartthrobs in their heyday, and they have the messy relationship timeline to prove it. The two were spotted together, on and off between 2011 and 2017. But things took a turn for the dramatic in 2016 when Bieber started posting photos with then-fling Sophia Richie. Fans (especially those who were rooting for Gomez and Bieber together) did not take the PDA -filled photos in stride, causing Bieber to threaten to turn his profile private.

Surprisingly, Gomez came to his fans’ defense. “If you can't handle the hate then stop posting pictures of your girlfriend lol – it should be special between you two only. Don't be mad at your fans. They love you," she commented, according to E! Online.

Bieber wasn’t willing to let a comment like that go. He replied in the comments section, “It’s funny to see people that used me for attention and still try to point the finger this way. Sad. All love.” Shots fired.

Gomez responded, “Funny how the ones that cheated multiple times, are pointing the finger at the ones that were forgiving and supportive, no wonder fans are mad. Sad. All love.” OK, that’s it. The next time I need to confront my ex, I’m ending the message with “Sad. All love.”

Bieber never addressed the cheating allegations directly, but he did post about his past relationship mistakes on IG in Sept. 2019. “I… abused all of my relationships. I [b]ecame resentful, disrespectful to women, and angry,” he wrote.

Clare Crawley and Dale Moss are happily back together now, but their breakup in early 2021 was definitely less-than-friendly. In Jan. 2021, Moss confirmed split rumors on Instagram. “I wanted to share with you all that Clare and I have decided to go our separate ways,” Moss wrote at the time. “We appreciate the love and support we've received from so many people, but this is the healthiest decision for both of us at this time. We strongly believe in leading with love and always remaining true to oneself — something our families have taught and instilled in us throughout our lives. We only hope the best things for one another.”

But, according to Crawley, she did not sign off on that statement. She responded with an IG post of her own, “I was made aware of a 'mutual' statement at the same time you all were, so I've needed some time to really digest this,” she alleged. “Speaking for myself, my intentions with this relationship have always been very clear, so the truth is I am crushed. This was not what I expected or hoped for and I am still trying to process this.”

You’d think a surprise breakup over IG would be impossible to get over, but the two got back together and went Insta-official once more in May 2021.

Kourtney Kardashian and Younes Bendjima dated from 2016 to 2018. After they broke up, Bendjima took his annoyance to Instagram, leaving a judgmental comment on one of her cheeky bikini photos. "That's what you need to show to get likes?" he commented. Rude.

Kourtney didn’t respond to his comment, but, in a March 2021 episode of Keeping Up With The Kardashians, admitted to Khloé Kardashian that she thought Bendjima was ultimately “negative” for her. No surprise then that Kourtney added that she “never” talks to him or responds to his texts. I wouldn’t respond to someone who commented that on my IG either.