Celebrity love lives are always a matter of interest; from tabloids to actual news channels, it’s all people seem to talk about! Why are we, as a society, so obsessed with the dating habits of celebrities? Some people think it’s because we like to live vicariously through them, while others believe it’s simply the enjoyment of saucy gossip!
Celebrities represent a sort of fantasy, and celebrity couples are no different, which is why we all love rooting for them and even shipping non-couples. Hollywood has many examples of actors and actresses finding their soulmates early on in their careers and still being together and happy. And while we adore these couples, they are not what we will be talking about today.
Some celebs just can’t seem to catch a break from drama when it comes to dating, and they are the ones we’ll be talking about today. Whether it’s on-again, off-again couples or love triangles, keep reading for our pick of celebs with the most dramatic love lives ever!
Saturday Night Live star Pete Davidson has quite a whirlwind dating history. He casually dated comedian Carly Aquilino for a while in 2015, but it was all quite low-key.
Pete also had an on-again, off-again relationship with Cazzie David for about two years. These two broke up for good in 2018, even though Pete told the media in 2017 that he was “very lucky” to have her.
Now, here’s where things get heated up. Pete announced his relationship with Ariana Grande publicly in 2018, but the two had known each other since 2016; around the same time he had started dating Cazzie! In fact, rumours had it that Pete and Ariana were already an item before breaking up with Cazzie.
Literally a month or so later, Pete was engaged to the God is a Woman singer. Both his exes poked light fun at his rushed decision, and the relationship itself did not last, with Pete and Ariana calling it quits after five months of being together (Pete would also go on to be a part of Thank U, Next, we’d love to add!).
Earlier this year, Pete was seen flirting with Kate Beckinsale, who is about twenty years older than him! The two had a fling that lasted a few months, during which they were also seen making out at a New York Rangers game.
Pete is reportedly open to finding love again and is not in a rush.
WWE star, Nikki Bella was married a long time ago before she even met John Cena. And get this, no one even knows who her husband was! All we know is that Nikki married her high school sweetheart in an impromptu Las Vegas ceremony (complete with uggs and an Elvis impersonator) when she was 20 and that the marriage lasted for a few years.
John is probably the only one who knows this guy’s name, besides Nikki’s family, because the public only found out when she told him on the show.
Nikki also dated another WWE star before John: Dolph Ziggler (aka Nicholas Nemeth). The two were together for around two years, but there have been rumours that Dolph still has feelings for Nikki. When Nikki and John were together, there was a Total Divas episode where Dolph tried to convince Nikki to take him back while John was in the ring!
Nikki and John were together the longest, but their relationship had many ups and downs. They split for good last year because of irreconcilable differences and have opted to remain friends.
Nikki has now confirmed that she is dating Artem Chigvintsev, who was her partner on Dancing with the Stars. We can’t help but wonder if Artem had something to do with Nikki and John’s breakup, because he was her partner while she was still with John, and there were rumours of John being very jealous.
Back in the nineties, Angelina was married to Jonny Lee Miller, and the pair divorced after a few years together. She has since reunited with Jonny while working with Peace One Day, a nonprofit organization they both support.
Angelina met Jenny Shimizu on the set of Firefox and claims to have fallen in love with her ‘the first second’ she laid eyes on her. Angelina was still married to Jonny when she met Jenny and said that if it weren’t for him then Jenny would have been the One.
Angelina dated Jenny for about three years. She then dated Timothy Hutton for two years after meeting him on the set of Playing God, but he reportedly broke her heart when he wasn’t as serious about the relationship as she was.
Angelina went on to marry Billy Bob Thornton in 2000, having met him on the set of Pushing Tin when he was still engaged to Laura Dern. After the two divorced in 2002, Angelina had short flings with Collin Farrell (whom she met on the set of Alexander) and Nicholas Cage.
There’s a very clear pattern here, which becomes even more obvious when we talk about Brad Pitt. Angie met him, again, onset (Mr. and Mrs. Smith) when he was married to Jennifer Aniston. The two got hitched in 2014 after many years (and kids) together, but unfortunately split two years later, after Brad reportedly cheated on her.
Being a teen star means being in the spotlight while you’re still growing up and learning about the ups and downs of dating. This is exactly what happened with Nick Jonas.
He dated fellow teen star Miley Cyrus for two years, starting when they were just 15! Miley later spoke about it, claiming that they were young and having fun but it wasn’t meant to work out.
Nick also dated another teen (and Disney star), Selena Gomez, soon after his split with Miley. This was a bit of an on-and-off relationship and created a juicy love triangle between these three heartthrobs.
Next, Nick dated singer Delta Goodrem, which was the first hint that he’s into older women, with Delta being eight years his senior. The relationship lasted for about ten months, after which Nick dated former Miss Universe, Olivia Culpo for two years.
This was one of his most publicized relationships, the only exception being his marriage. Nick also dated Kate Hudson (who is fourteen years older than him), claiming that they had “an unbelievable connection.” After this, Nick had short flings with Lily Collins and Georgia Fowler.
Nick met Priyanka Chopra (eleven years his senior) last year. The two got married after about six months of being together, and seem to be very happy indeed!
Kristen Stewart has dated quite a few people that she has worked with, the very first being Michael Angarano, who she met on the set of their indie film Speak. The couple called it quits in 2009 before Kristen moved on to The Twilight Saga, which would not only be her first big franchise but the grounds for her first big romance as well.
Kristen dated real-life Edward aka Robert Pattinson for more or less five years, but she also cheated on him with Rupert Sanders, the director of Snow White and the Huntsmen, in 2012.
Paparazzi pictures resulted in Kristen getting caught in the act. Robert was heartbroken but decided to forgive her. However, things were never quite the same between those two as they broke up for good the following year.
Kristen dated Alicia Cargile on-and-off for a few years, during which time Kristen also spoke about being more comfortable with dating women. She also had flings with Lynn Gunn (vocalist of Pvris) and French artist Soko. There were even rumours of her having been with Dakota Fanning at some point!
Kristen’s next serious relationship was with Annie Clark aka St. Vincent, with whom she broke up a few years later. Kristen is currently dating Victoria’s Secret model Stella Maxwell. Things seem to be pretty serious between these two, especially since they moved in together after just five months of dating!
Taylor Swift has, arguably, the most dramatic love life in Hollywood. Infamous for all her songs about her exes, we thought it was worthwhile to take a look at some of them.
Taylor’s first public romance was with Joe Jonas in 2008, which did not end well, with him breaking up with her over the phone. She then dated Taylor Lautner for a few months, after meeting him on the set of Valentine’s Day.
Taylor also dated John Mayer, who has even more famous exes than she does! Their ill-ending romance was immortalized with her song Dear John. After this breakup, there were rumours of Taylor dating the late Glee star Cory Monteith.
Taylor then went on to have short (lasting just a few months) relationships with Jake Gyllenhaal, Conor Kennedy, and even Harry Styles. All of these relationships seemed serious at first, but did not work out ultimately.
Calvin Harris was Taylor’s next beau, and the one she dated the longest so far. The two seemed like a happy couple before they split up abruptly after a year. Just two weeks after this breakup, Taylor Swift began a short fling with Tom Hiddleston.
After splitting up with Tom in 2016, Taylor was single for a while before she met her current boyfriend, Joe Alwyn. These two have been together for two years, and things seem to be getting more and more serious, so we really hope Taylor has found her soulmate!
The Weeknd, aka Abel Tesfaye, has had some dating drama with two women in particular: Selena Gomez and Bella Hadid.
In 2015, it became official that Abel was dating Bella Hadid. His music video In the Night, in which Bella also starred, came out the same year. The following year, these two made their red carpet debut at the Grammys, where he also won. Later that year, they broke up but remained friends.
It was confirmed that The Weeknd was dating Selena early in 2017 and he even mentioned her in his song Party Monster.
A few days after this confirmation, the petty drama began, ranging from shade-throwing with even Hailey Bieber (a friend of Bella’s) getting involved, and a lot of unfollow-ing.
Things seemed to be going well though. Abel even scheduled his 2017 tour around Selena’s kidney donation surgery so he could be there for her!
But this pair split at the end of 2017, after Selena’s reported reunion with Justin Bieber. Soon afterward, Abel was reportedly back with Bella, even being seen kissing her in public.
They confirmed this in July 2018, moved in together, and sparked rumours of being engaged because of how well things were going.
Unfortunately, Bella and Abel called it quits once again this year, just when everyone had been rooting for them.
Another teen star, Justin Bieber had a lot of flings before he settled down with Hailey Baldwin. The list is long, so let’s dive in!
Caitlin Beadles is the first known girlfriend of Justin, whom he dated at the beginning of his fame. He was also linked to Jessica Jarell soon after, but a relationship was difficult because of his new schedule.
In fact, most of Justin’s love life (that we know of) is based on rumor alone, which makes it all the more exciting. He is also rumored to have been involved with Miranda Kerr. All we can say is, Orlando Bloom (her then husband) probably didn’t try punching him for no reason!
Justin was also supposedly involved with two other Victoria’s Secret models: Barbara Palvin and Adriana Lima! While Barbara has never commented on this, Adriana denies any involvement.
Justin briefly dated Sofia Richie. The irony here is that he would also go on to have a fling with Kourtney Kardashian, whereas Sofia would go on to date Kourtney’s ex, Scott Disick!
Some other women that Justin has dated include Nicola Peltz, Paolo Paulin, and of course, Selena Gomez, with whom he had an on-and-off relationship for years, even going so far as to throw shade on The Weeknd when Selena was dating him.
Justin dated Hailey for a year before his 2017 reunion with Selena, and then for another year after breaking up with Selena, which resulted in him marrying her and making her Hailey Bieber.
Is Kim Kardashian any stranger to drama? Of course not. Drama, controversy, rumours; the reality star seems to be familiar with them all. Now married to Kanye West and mother of his four children, she went through a lot more before settling down.
Kim eloped with music producer Damon Thomas to Las Vegas in 2000, long before she became famous. The two divorced four years later, after which she dated Ray J, the man with whom she made her infamous sex tape that was later leaked.
She met Ray J while still married to Damon, and some of her fame is attributed to her sex tape with him. After breaking up with him in 2006, she went on to date Nick Cannon, who broke up with her a few months later, claiming that it was because she lied and denied the existence of her sex tape, despite calling her “one of the nicest people you’ll ever meet.”
Kim then had an on-and-off relationship with Reggie Bush that lasted about three years. She also had a brief fling with Miles Austin. Kim married NBA star Kris Humphries in an extravagant televised wedding in 2011 and filed for divorce after just 72 days, which led to people calling the marriage a publicity stunt.
Soon after, Kim began to date Kanye. The two had been friends for about a decade but only started dating in 2012. They soon got married, and are now a happy family of six.
Orlando Bloom is probably the most surprising name on this list. The British actor seems pretty low-key, but he is quite the hopeless romantic, and claims to be “completely in love with the idea of love.”
Orlando’s first public relationship was with Kate Bosworth in 2004, when he was constantly torn between keeping his relationship private and gushing about her to the media. Two years later, the two decided it would be best for them to part ways.
There were also rumours of Orlando dating Lindsay Lohan and Penelope Cruz, but these were never confirmed.
In 2007, Orlando began dating Victoria’s Secret model Miranda Kerr. It was reportedly love at first sight, and they got engaged a couple of years later. The couple wed in a private ceremony in 2010 and had a son, Flynn. Unfortunately, Miranda and Orlando split in 2013, despite remaining amicable and respectful towards one another.
Orlando also reportedly dated Selena Gomez amidst her on-and-off relationship with Justin Bieber (who is rumoured to have hooked up with Miranda). This led to a physical fight between Orlando and Justin as well!
It was in 2016 that Orlando started dating Katy Perry, but they also split briefly in 2017 before reuniting in 2018. The rest is happy history; Orlando proposed with a 5 million dollar ring this Valentine’s Day, and she said yes!
Megan Fox is quite the sex symbol in Hollywood, which has always led to curiosity about her love life. But the predominant drama in Megan’s love life has been due to one man only: Brian Austin Green, and that is what sets her apart from everyone else on this list.
The on-again, off-again relationship between these two lasted well over a decade; beginning with what some might call bad signs (Brian fifteen years her senior, and she on the brink of becoming famous) in 2004.
The couple was engaged in 2006, just a year before Megan’s breakthrough role in Transformers. The engagement broke off in 2009 for various reasons. Scheduling issues meant that the couple was growing apart, and Megan felt she was too young to be married. It was also around this time that she hooked up with co-star Shia LaBeouf.
Brian and Megan got re-engaged just the following year and married in a private ceremony. They then went on to have two kids (with Brian having a son from his previous marriage as well), but things were starting to get complicated with the couple reportedly having intimacy issues.
Brian and Megan separated and filed for divorce in 2015, but they began to put an effort into making things work soon after, so they got it cancelled in April 2019. Megan spoke to the media saying that there will be no more splits and that Brian is her “soulmate.”
Miley Cyrus has been making headlines not only as a teen star, but also as a rebellious twenty-something woman trying to outlive her Disney image. Miley’s first ‘boyfriend’ was Tyler Posey when he was 9 and she was 7! He was even her first kiss! Does this count? We’re not sure, but it sure is adorable.
Miley dated Dylan Sprouse in a similar way when she was about 11, but her first long term relationship was with Nick Jonas in 2006. The two were still fairly young though, and things ended after a year. Miley then dated Justin Gaston, a reality star five years her senior, for about nine months.
It was in 2010 that Miley met Liam Hemsworth, on the set of Nicholas Sparks’ The Last Song. The two dated for a while before getting engaged in 2012. They split a year later, but we all know that wasn’t the end.
Before getting back with Liam, Miley sparked rumors of dating Justin Bieber (which were false) and Jared Leto. She also dated Liam’s old friend Kellan Klutz for a while. She also had short flings with Patrick Schwarzenegger and Stella Maxwell.
Miley and Liam reconciled two years after their initial split, then separated again for a while before getting married in 2018. Unfortunately, the couple has now announced that they are separating after less than a year of marriage.