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Get ready for a wild ride through the love lives of some of Hollywood’s most talked-about stars. From whirlwind marriages to headline-grabbing romances, these celebs have dating histories that are as unpredictable as they are fascinating. Whether it’s Britney Spears’ rollercoaster of relationships or Leonardo DiCaprio’s string of high-profile flings, we’re diving deep into the tangled webs of love and heartbreak that keep the gossip mills buzzing.
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00:00Pete was famously engaged to Ariana Grande, dated Kate Beckinsale, and most recently is linked to Bridgerton's Phoebe Denever.
00:07Welcome to Ms. Mojo, and today we're exploring 10 celebs with the most jaw-dropping romantic resumes.
00:13It was always on again, off again. And I went back close to nine times.
00:21Britney Spears. Often described as the princess of pop, Britney Spears' love life has been a full-blown Hollywood rollercoaster.
00:27Who else starts dating Mario Lopez, slides to Robbie Carrico, and then jumps into a culture-shaking romance with Justin
00:34Timberlake all before 23?
00:36What goes around, comes around. In her memoir, obtained by the New York Times before its official release, Britney confirms
00:43she cheated on Justin, kissing choreographer Wade Robson.
00:46Just when you think she might slow down, Britney shifts gears, flings with Wade Robson, Fred Durst, and Colin Farrell.
00:52Quote, brawl is the only word for it. We were all over each other, grappling so passionately, it was like
00:59we were in a street fight.
01:00It's mud. It's a zoo.
01:02Then came the whirlwind, her infamous 55-hour Vegas marriage to Jason Alexander, followed months later by her high-profile
01:09saga with Kevin Federline.
01:10She writes on X, formerly Twitter, October 15th,
01:13The constant gaslighting from my ex-husband is extremely hurtful and exhausting.
01:18Let's not forget her flings with paparazzo Adnan Ghalib and agent-turned-fiancé Jason Trawick, and even another marriage to
01:25Sam Asghari.
01:26Britney was definitely busy, and her lineup is explosive, unpredictable, and impossible to ignore.
01:32After a so-called nuclear argument, in which he accused her of cheating.
01:36But today there are reports that Britney is adamant that she never cheated, and the two haven't gotten along for
01:42a while.
01:43Billy Corgan
01:43The love life of Smashing Pumpkins frontman Billy Corgan is almost as wild as his music.
01:48In 1991, he orchestrated a meeting with Courtney Love after spotting her photograph on Hole's new single.
01:54Five songs out of 12, Billy came in and helped me, mostly with vocals.
01:59But the relationship ended when she discovered he was seeing someone else.
02:02He then married Chris Fabian in a quiet ceremony, only to separate two years later, calling the marriage unhappy.
02:08Next came a nearly decade-long romance with Yelena Yumchuk, followed by a short-lived fling with Emily Autumn.
02:14There was even a brief Hollywood Hills chapter with Love, before he was later linked to pop stars Jessica Simpson
02:20and Jessica Oraglaso.
02:21Sort of explains things.
02:23That's such a surprise.
02:23And someone else who doesn't quite get the relationship is Billy's ex, Courtney Love,
02:28who has been texting him, what are you doing with Simpleton?
02:31Finally, he found steady ground with Chloe Mandel, whom he married in 2023.
02:36Corgan's dating saga surely hits every note.
02:39And you've been together 10 years, and you have two children together, and what happened?
02:43You finally proposed?
02:44Did you get down on one knee and say, Chloe, I've been a fool.
02:50I'm in love with that.
02:52Katy Perry
02:52Are you even surprised Katy Perry is here?
02:55Her dating history may be slightly tamer than some, but it is packed with high-profile romances.
03:00In the mid-2000s, she dated Sons of Anarchy actor Johnny Lewis.
03:04Then came Travi McCoy, whose breakup led to Circle the Drain.
03:08You say that you love me.
03:11It won't remember in the morning.
03:14A Josh Groban rumor floated around in 2009, but neither of them confirmed anything.
03:19Then came the big one, her intense marriage to Russell Brand that burned out fast and gave us one of
03:24her most emotional songs.
03:26They've been having trouble, and that their marriage may be on the rocks.
03:29She kind of debunked it a little while ago, but now it looks like that could be the case.
03:34After that were quick sparks with Robert Aykroyd, John Mayer, Diplo, and even a rumor of something with Jared Leto.
03:40We have music as an understanding and love between each other, and we connect.
03:45In 2025, her long-term relationship with Orlando Bloom ended, only to be followed by a very public tryst with
03:52former Canadian Prime Minister Justin Trudeau.
03:54It's never boring with Katy.
03:56They're enjoying each other's company.
03:57Katy likes that Justin is flirtatious, smart, and successful.
04:01Charlize Theron
04:02When it comes to Charlize Theron's love life, let's just say even Hollywood scriptwriters would take notes.
04:07She kicked things off with actor Craig Bierko in the mid-90s.
04:10Then she moved on to musician Stephen Jenkins.
04:13And yes, a rumored fling with George Clooney popped up in 2000 right in between.
04:17My time is opening up a little bit more.
04:19A little bit.
04:19So you're opening yourself up emotionally to perhaps being in the great love of your life.
04:24Yes, totally.
04:25I mean, no pressure.
04:26From 2001 to 2009, she dated Stuart Townsend, a relationship that ended when they figured it had run its course.
04:33Charlize Theron walked through a sea of adoring fans.
04:36Her boyfriend, Stuart Townsend, a few steps ahead.
04:39Townsend wrote and directed Battle in Seattle, which features Theron in a prominent role.
04:44Along the way, there were sparks with Keanu Reeves and whispers about flings with Jeremy Renner, Ryan Reynolds, and Alexander
04:50Skarsgård.
04:51Then, Sean Penn held her heart from 2013 to 2015.
04:55They allegedly got engaged, but ultimately it wasn't meant to be.
04:58Tying the knot?
05:00Us Weekly claims Charlize Theron and Sean Penn are engaged.
05:04The magazine quotes an anonymous source who says Penn popped the question in Paris in November.
05:10John Mayer.
05:11It would appear that John Mayer has not only dominated Hollywood with his music, but with his love life too.
05:16First, there was Jennifer Love Hewitt with that early fame romance in 2002, before moving on to Jessica Simpson.
05:22He might be the one that won't like to read this book very much.
05:27No, no.
05:28In the mid-2000s, Mayer was seen with Minka Kelly, keeping his dating life firmly in the spotlight.
05:33From there, Jennifer Aniston entered the picture, a relationship that made headlines and had fans swooning.
05:39The paparazzi snaps ignite some serious questions as to whether the exes just happen to be at the popular establishment
05:45at the same time, or if they dine together.
05:50Then, in 2009, came a highly publicized fling with Taylor Swift, and later a relationship with Katy Perry, another pairing
05:57that captured media attention.
05:58He believes Swift's song is about him, and it hurts.
06:02Telling the magazine, quote,
06:03It made me feel terrible because I didn't deserve it.
06:06It was a really lousy thing for her to do.
06:09Through all the ups and downs, Mayer's relationships have been as candid and compelling as his lyrics.
06:14Even now, he seems to be searching for deeper, more meaningful connections.
06:18Taylor Swift, Jennifer Aniston, Jessica Simpson.
06:24The first, this is the...
06:27I think it's double jeopardy, actually.
06:30Grace Kelly
06:30Before she became Princess of Monaco, Grace Kelly was already a force, captivating hearts across Hollywood and beyond.
06:38Enjoy a look through Grace Kelly's life and her journey in becoming a princess through her precious memories.
06:44The acclaimed actress charmed some of the biggest stars, having flings and relationships with Gary Cooper, William Holden, and Clark
06:51Gable.
06:51She even had a serious engagement with fashion designer Oleg Cassini, which never resulted in marriage.
06:57She was reportedly friends with Frank Sinatra and briefly linked to Tony Curtis and Ray Moland.
07:02That's the champagne for you.
07:04They're not putting bells in the bubbles.
07:09You're quite a fella.
07:12That's what they say.
07:13Each romance and each whispered connection painted a picture of a woman who lived boldly, both on and off screen,
07:19adding to her mystique.
07:21But here's the twist.
07:22She traded all that glitz for royalty, marrying Prince Regnier III in 1956.
07:27Though Grace has passed, her enchanting allure remains undeniable.
07:31Was she the most beautiful thing you'd ever seen?
07:34Well, surely, yes.
07:38I think probably it was very obvious.
07:42Scarlett Johansson.
07:43Honestly, when you look at Scarlett Johansson's dating history, her 2017 Playboy interview about monogamy suddenly makes perfect sense.
07:50Her romantic journey started with her high school sweetheart Jack Antonoff back in 2002.
07:55Soon after came her first major confirmed relationship with Josh Hartnett, lasting from 2005 to 2007.
08:01Then, Ryan Reynolds stole her heart, and they got married in 2008.
08:05Their marriage ended three years later as she wasn't ready for that level of commitment.
08:10The exes were married from 2008 to 2011, but have both long since moved on.
08:15Brief sparks with Sean Penn followed, and by 2012, she had moved on to Romain Doriac, with whom she had
08:22a child before they divorced in 2017.
08:24The actress and the journalist have reportedly been separated for months, and Scarlett stepped out over the weekend at the
08:30Women's March in D.C. without a wedding ring.
08:33The couple share one child, two-year-old daughter Rose.
08:37While she had plenty of rumored flings between her past relationships, today, Scarlett is married to Colin Jost, keeping things
08:43simple.
08:44It's a very special moment, and, you know, I think more than anything, when someone tells you they want to
08:48share the rest of their life with you, and that just is a lovely, special thing.
08:54Ben Affleck. One thing about Ben Affleck? His love life has absolutely played out like a Hollywood romance miniseries.
09:01The saga kicked off with his on-and-off spark with Gwyneth Paltrow, a relationship that set the tone for
09:06the spotlight.
09:07Thanks for your support. It's terrific.
09:09You want me to leave?
09:11No! What do you... No.
09:13Are you sure?
09:14No, yeah, I mean, no, I'm thrilled that you're here.
09:17Then came the infamous Bennifer era, an engagement with Jennifer Lopez in 2002 that crumbled under media frenzy by 2004.
09:25After the dust settled, Affleck slipped into something steadier with Jennifer Garner.
09:29Our marriage is the work of love. What would you have called it in a speech?
09:33A gift. I would have said thank you to my wife. Our marriage is a gift.
09:36He married her in 2005 and welcomed three kids before their split in 2018.
09:41Another source explained,
09:43They have a mutual understanding that their children come first and are committed to that.
09:49Then came a few post-divorce rebounds from Lindsay Shuchas to Ana de Armas, until fate circled him back to
09:55Lopez.
09:56Yep, Bennifer 2.0 reignited in 2021 and they married in 2022.
10:01But even that fairy tale couldn't hold forever.
10:04On the demise of Bennifer 2.0, quote,
10:07My temperament is to be a little bit more reserved and private than hers.
10:12Leonardo DiCaprio.
10:13Where do we even begin with Leo DiCaprio?
10:16The Titanic star hasn't just conquered the box office.
10:19He's also made headlines for his numerous high-profile romances.
10:22From his early days, Leo was linked to a string of models and actresses, including Giselle Bündchen and Bar Raffaelli.
10:29Was I alone in wanting to do some serious soul-searching while he stayed the same?
10:33In the end, unfortunately, the answer was yes.
10:37Yikes.
10:38These relationships captured attention because of the notable age gaps, but he didn't seem to care.
10:43He kept the trend alive, from whirlwind flings to multi-year love affairs with Blake Lively, Camila Marone, and Tony
10:49Garn, among many others.
10:51He's dating this girl by the name of Tony Garn, and being that Leonardo DiCaprio won't walk down the aisle,
10:56she's like, listen, I want a movie career.
10:58Stat.
10:58He always seemed to date younger stars at the prime of their careers, and was even briefly linked to Rihanna.
11:04Romance rumors have been swirling around Leo and Rihanna for months now, but both stars denied a relationship in March.
11:12Most recently, he's in the spotlight with model Vittoria Ceretti, proving Leo's magnetism has not faded.
11:18The notoriously private couple skipped posing on the red carpet together.
11:22The two have been linked since 2023, but keep a low profile.
11:27Before we unveil our top pick, here are some honorable mentions.
11:31Alex Pettifer.
11:32He had multiple high-profile relationships with co-stars.
11:35Where was our first kiss?
11:41That means he forgot.
11:42Oh, on the dark side of the moon.
11:44I know it was in Poland.
11:45Amanda Seyfried.
11:46Her search for love left many exes.
11:48But pretty long.
11:49I mean, she's, yeah.
11:51Feels like a long time.
11:52Okay.
11:53No, but yeah, we do everything together, but we don't do much.
11:56So between, like, a month and five years?
11:58Somewhere between there?
11:58Yeah.
11:59Rachel McAdams.
12:00She dated lots of famous actors.
12:02I knew he was going to be a gen- I mean, I was pretty sure he was going to
12:06be a gentleman
12:06and, uh, you never know, but...
12:10Halle Berry.
12:11She has had many confirmed relationships, including three marriages.
12:15How does it feel to do this together?
12:18Well, it feels better now I'm going to hold her hand.
12:20It feels better.
12:21Oh, well, we've been doing this for five years together, so this is, like, the longest relationship
12:26I've ever had.
12:27Kate Hudson.
12:27It's been a long journey of finding love.
12:29I hope something's happening, even if it's casual.
12:32I don't- I- I don't like addressing any kind of gossip and stuff.
12:37Lovey gossip.
12:38No.
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12:53Pete Davidson.
12:54We know you were all expecting this one.
12:57Pete Davidson's dating life has been all over the place.
12:59Literally.
13:00After being with Carly Aquilino, he moved to Kazzy David.
13:03But things really blew up when Ariana Grande entered the picture.
13:07Ariana spent the majority of the night hanging out with her.
13:09Seemingly reacting to the engagement news today, Ariana tweeted,
13:13I love you, along with several monkey emojis.
13:15They got engaged in a high-voltage romance that ended just a few months later.
13:19After that heartbreak came a string of Hollywood flings with Kate Beckinsale,
13:23Margaret Qualley, Kaya Gerber, and Phoebe Denever.
13:26Then the world watched him spark with Kim Kardashian after that headline-grabbing SNL moment.
13:30Now, are you gonna kiss me or not?
13:32I sure am, Jasmine.
13:36He also recently ended things with Chase Suey Wonders and Madeline Klein,
13:40and is currently dating Elsie Hewitt, with whom he has a child.
13:44So, what's next for Pete?
13:45Another whirlwind, or is he finally settling down?
13:48The comedian and his girlfriend, Elsie Hewitt,
13:50celebrated their baby-to-be with a bunny-themed baby shower.
13:54Honestly, I couldn't be more excited.
13:56The baby's mother is one of my favorite people to ever exist, ever.
13:59Which of these celebrities has the wildest dating history?
14:02Let us know in the comments section.
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