The Weeknd's Up-And-Down Love Life

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The Weeknd's provided plenty of music for romantic occasions -- "Earned It," anyone? -- and his love life's been as dynamic as his songwriting.

The hitmaker's dating experience has seen him link up with some of the buzziest names in the entertainment world ... both in the short and long runs.

Here's a look at some of the biggest names the songwriter's been connected to over the course of his career.

The Weekend Began Dating Bella Hadid After He Tried To Work With The Model

One of The Weeknd's most high-profile relationships was with supermodel Bella Hadid, who he first met when he asked her to appear in the artwork for his album "Beauty Behind The Madness."

The pair first set off the rumor mill when they were spotted together at the 2015 Coachella festival, and they made their red carpet debut at the 2016 Grammy Awards.

The Weeknd -- born Abel Tesfaye -- and Hadid remained together for several months, and although they ultimately separated in November 2016, a source told People at the time the two still held "a great deal of love for one another."

The pair went on to reunite -- on strictly professional grounds -- at that year's Victoria's Secret Fashion Show, during which the singer performed while his ex walked the runway.

A source spoke to E! News and revealed Bella had approached her former partner at a restaurant prior to the event, and the former couple was "really cool with each other."

The Weeknd Had A Whirlwind Romance With Selena Gomez

The Weeknd's love life didn't stop there, as he subsequently started seeing Selena Gomez, whom he had performed alongside during the 2015 Victoria's Secret Fashion Show.

While the pair's romance didn't kick off in earnest for another two years, they made sure their fans were well aware of their connection, as they went Instagram official in April 2017.

Oh yeah, and in case that wasn't enough proof for their respective fanbases, they decided to lock lips at that year's Met Gala.

The thing is, Hadid was pretty upset by the singer's willingness to move on from their relationship ... and an insider told People at the time the model was "hurt and pissed" by The Weeknd's actions.

The model didn't have to remain upset for too long, though, as the singers went their separate ways in October of 2017.

The split, however, was apparently amicable, and Gomez claimed she remained "best friends" with The Weeknd in an interview with Billboard.

The Weeknd Reunited With Hadid ... For A While

The Weeknd appeared to run right back to Hadid following his split from Gomez, as he was seen leaving her apartment in November 2017 ... after which a source told People that, while they were "not back together," the singer had "never stopped loving" the supermodel.

The pair set off more rumors when they were seen together at the 2018 Coachella festival, and they sent their fans into overdrive when they kissed at that year's Cannes Film Festival.

The Weeknd and Hadid were later spotted in each other's company stepping out on several occasions over the course of 2018 -- but they kept quiet about their romance.

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Sharing A Smooch!

The two remained together until August 2019, when they decided to split up for the second time.

Rumors about a potential reconciliation began to swirl after The Weeknd attended Hadid's 23rd birthday party that October ... although our sources told us they had stayed on platonic terms during the event.

The Weeknd Appeared To Move On With A DJ

The singer was next linked to Simi Khadra, and we shared a video of the pair kissing during his 32nd birthday party in Las Vegas.

It's also worth noting the DJ, as well as her twin sister Haze, were friends with both Hadid and Gomez ... funny how life works out like that sometimes!

While a source told People The Weeknd was "not in a committed relationship with anyone" at the time, the pair kept tongues wagging, especially after they were pictured together at the 2023 Cannes Film Festival.

The singer also made a reference to having a "girlfriend" -- whom he did not name -- in an interview with the New York Times, and claimed the girlfriend's favorite scene in his film "Hurry Up Tomorrow" was the one where he was hit by a champagne bottle.

Oh yeah, and we shared that Khadra accompanied The Weeknd to the film's premiere party in May 2025.

'Love Island USA' Iris and TJ Back Together?!?

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BIG HUGS ALL AROUND!!!

"Love Island USA" contestants Iris Kendall and TJ Palma look like they may be giving things another shot back home on the mainland ... because she's hanging out with him, and not Pepe Garcia.

TMZ obtained video from Iris and TJ's reunion Monday night in Los Angeles ... they were coupled up in Fiji before TJ got eliminated -- now they've reunited in L.A. and it looks like the sparks are flying.

Check out the clip ... Iris and TJ are hugging, smiling and flirting ... and we're told they went on a walk and talk for about two hours before going into his place, where they were greeted by fellow 'Love Island' contestant Austin Shepard.

Jessica Alba Mystery Man Revealed -- Actor Danny Ramirez

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The mystery man who accompanied Jessica Alba to Cancun is none other than Danny Ramirez, TMZ can reveal.

Alba and the actor boarded a plane in Cancun -- where they had spent time together -- and headed back to L.A. on an American Airlines jet.

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BREAKING THE BIG NEWS!!!

The pair left Cancun shortly after 5 PM Sunday and landed in L.A. at 7:45 PM.

Sofia Vergara's Dating History

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Sofia Vergara's made a name for herself by flaunting her flawless physique on the small screen ... and you gotta imagine she's piqued the interest of plenty of guys!

Turns out that's a fact, as the "Modern Family" actress has had quite the love life, which has involved both marriage -- marriages, actually -- motherhood, and plenty of boyfriends.

We're going to take a look back at who the performer's been linked to in her past ... as well as the people who've put a ring on her finger -- at least for a while.

Sofia Had A Kid When She Was Just 19

Vergara's love life stretches all the way back to her teenage years, as she married her first husband -- and high school sweetheart -- Joe Gonzalez when she was just 18.

The pair went on to welcome a son named Manolo after the actress turned 19, and she later told People she found the fact she "kind of grew up together with my son" to be a positive thing in her later years.

Vergara and Gonzalez amicably went their separate ways after two years of marriage ... she told Parade her ex-husband would stay at her house during his visits to the United States.

The actress was later linked to nightclub owner Chris Paciello, who she met after she moved from her native Colombia to Miami, Florida.

However, Vergara's romance with the nightlife figure didn't last, and the pair ultimately broke up.

Sofia Had A Legal Battle With Her Former Fiancé

The actress eventually began seeing businessman Nick Loeb, who she started dating in 2010.

The pair dated for two years before they decided to get engaged in 2012, and the actress froze several of her embryos the following year in anticipation of welcoming another child via surrogate.

However, Vergara and Loeb shocked her fans when they abruptly called off their engagement in 2014 ... and they subsequently began a legal dispute regarding the status of the frozen embryos.

According to People, the actress filed a set of legal documents in California, hoping to block her former fiancé from utilizing the embryos if he did not obtain her written consent.

A request for a permanent injunction was granted, and Loeb was restricted from using the embryos "to create a child without the explicit written permission of the other person," according to court documents.

Vergara Embraced Married Life Again ... For A While

Vergara moved on with actor Joe Manganiello, who she met at the 2014 White House Correspondents' Association Dinner, following her separation from Loeb.

The pair only dated for a few months before they announced their engagement that December, and they went on to make things official in a wedding ceremony in 2015.

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Vergara and Manganiello remained together for nearly a decade in July 2023 before they announced they were planning to separate.

The actor filed for divorce that same month, and we revealed they'd settled their divorce in February 2024.

Vergara opened up about her split in an interview with Spanish newspaper El País, claiming Manganiello wanted to start a family with her -- but she didn't "want to be an old mom."

Vergara Embraced Being Single ... And Dated A Surgeon

The actress dusted herself off following her divorce and moved on with orthopedic surgeon Justin Saliman, with whom she was first spotted in October 2023.

The surgeon appeared in several photos and videos on the actress' Instagram account over much of the following year.

However, Vergara alluded to a split with Saliman while speaking to Access Hollywood at the 2025 Golden Globes ceremony ... she claimed she was manifesting "a boyfriend, or a lover, maybe" for the new year.

The actress set off the rumor mill when she was spotted with Tom Brady in several photos taken during a star-studded yacht trip in Spain in July 2025.

However, our sources told us the pair's connection was apparently just a summer fling ... sorry, folks!

Bella Hadid's Dating Life

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Bella Hadid has made a name for herself strutting down runways all over the world ... and for the ups and downs in her love life!

The supermodel has been connected to some pretty buzzy -- and low-key -- boyfriends over the course of her life ... and we've seen her move from the bright lights of New York City to the wide plains of Texas.

Here's a look at how the fashion industry powerhouse navigated her love life ... before she decided to settle down with a cowboy.

Hadid Was Linked To The Weeknd Early In Her Career

Hadid's buzziest relationship was with musician The Weeknd, who first reached out to the model in an effort to get her to appear on the cover of his 2015 album, "Beauty Behind The Madness."

Although she didn't end up on the cover, sparks began to fly between the two ... and they made their red carpet debut at the 2016 Grammy Awards ceremony -- after being spotted on several PDA-filled outings.

Hadid subsequently spoke about her experience at the awards event in an interview with Glamour, saying, as "a girlfriend I wanted to be there to support" her boyfriend at the time.

The pair remained together until November 2016, when a source spoke to People and claimed they'd decided to go their separate ways.

The source said, despite the split, Hadid and The Weeknd -- born Abel Tesfaye -- still had "a great deal of love for one another" and would "remain friends."

She Ended Up Reuniting With The Weeknd ... For A While

The model and the singer -- who later dated Selena Gomez -- remained apart until November 2017 ... when he was seen leaving her apartment in New York City.

They went on to spark further reconciliation rumors during the following year's Coachella Festival, and they were seen locking lips at the 2018 Cannes Film Festival.

Hadid and The Weeknd coordinated outfits for his 29th birthday party in February 2019, and an onlooker told People the two openly packed on the PDA at the event.

The pair remained together until that August, when a source spoke to E! News and claimed they had separated for the second time.

The source added while the pair seemed open to a future reconciliation, they were committed to "focusing on themselves and their projects."

Hadid Embarked On A More Low-Key Romance Following Her Breakup With The Weeknd

Hadid focused on herself for just under a year, before she secretly began seeing art director Marc Kalman, according to Page Six ... the two were first spotted leaving a cafe together in New York City in July 2020.

The two tried to keep their romance under wraps, though, and the news about their romance wasn't revealed to the public for a full year.

Hadid began opening up more about her relationship with Kalman in 2021, and he started being featured in photos shared on her Instagram account.

The model and the art director -- who were then seen in each other's company in various public outings -- remained together for another two years ... before they called off their romance.

A source gave a bit of insight into the pair's breakup to Entertainment Tonight, claiming while the split was "amicable," their relationship "ran its course."

She Eventually Found Love ... With A Cowboy!

Hadid didn't stay single for long ... we spotted her making out with cowboy Adan Banuelos on a trip to Fort Worth, Texas, in October 2023.

The model -- who bonded with the equestrian over their shared love of horses -- hard-launched her relationship with Banuelos, sharing a photo of him on her Instagram account on Valentine's Day in 2024.

Hadid later told British Vogue she met her boyfriend on a trip to the Lone Star State in 2023, and quipped she "always wanted the cowboy."

She said her first meeting with Banuelos felt like "a gust of fresh air" and added the cowboy is "pretty gorgeous" ... How's that for head-over-heels?!

Oh, and it looks like she's in it for the long run, as we revealed she'd picked up a property in the Fort Worth area last year so she could mosey on over to her boyfriend's place whenever she liked!

Jessica Alba Flying High With New Mystery Flame!!!✈️

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Looks like Jessica Alba’s love life is taking off again -- 'cause she's jet-setting with a mystery man as she and Cash Warren still hammer out their divorce.

Check out these clips TMZ obtained of Jessica and her mystery man boarding an American Airlines flight together at 5 PM Sunday, flying from Cancun to LAX.

Jessica rocked a baseball hat and shades, and even used her passport to cover her face for a sec -- so, it seems like she's keeping it low-key for now.

Casey Anthony Old Flame Has Advice For New Man ... Good Luck, Bud!!!

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A guy who had a quick fling with Casey Anthony is weighing in on her latest romance with a former cop ... saying he feels no ill will toward her despite cutting things off once he found out about her infamous murder trial.

Antony Karagiannis -- who hung out with Casey a couple times back in 2018 -- tells TMZ ... he hasn't kept tabs on Casey's budding relationship with New Hampshire gun store owner Ben Beauchemin ... but he shared a short and sweet message to them -- "Good luck to both of them." Karagiannis says he hopes Casey finds peace and happiness "with whatever she has left in her life."

As for their relationship, Karagiannis makes it clear he and Casey were never an item -- just two people who casually hung out -- and had a one-night stand.

Ben Beauchemin Who's Casey Anthony's 'Situationship' Partner?

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Casey Anthony set off the rumor mill earlier this week when she was spotted on what appeared to be a date with a mystery man in New Hampshire.

And we've since revealed the name of the dude is Ben Beauchemin -- turns out he's got a bit of a past, too.

We're going to take a look into this guy's background and get a better picture of who the media figure -- who was found not guilty in 2011 of killing her 2-year-old daughter Caylee -- hung out with on Wednesday night.

He Was Born And Raised In New Hampshire

Beauchemin must've felt pretty comfortable hanging out in his home state, as he says he's lived in New Hampshire his entire life in a video produced for the New York Times.

Beauchemin described himself as an Army veteran in the video, and he's also worked as a police officer in the past.

We've been told that he comes from a sizable family -- although none of them were apparently aware that he had met Anthony.

A family source also told us that Beauchemin stopped responding to his family and took down his Facebook page after we revealed he'd been out with Anthony.

His family members were also apparently unaware he had gone to dinner with Anthony, or that they had even connected.

He Owns And Operates A Gun Store

Beauchemin's the owner of Wicked Weaponry, a gun store located in Hooksett, NH.

He's been open about the politically divisive aspect of working in the arms industry, and he described himself as a "liberal" who happens to "really love the Second Amendment."

The former cop told the New York Times he's often apprehensive about telling his left-leaning friends that he owns a gun store, and listed "women's rights, reproductive rights, and the economy" as his main political concerns.

Beauchemin -- who told New Hampshire Public Radio he'd been using guns ever since he was "five or six years old" -- admitted his political beliefs factor into his business practices ... and he claimed he likely wouldn't sell bump stocks in his store following the events of the 2017 Las Vegas mass shooting.

He said he wanted the arms world "to self-regulate as a gun industry, as a gun culture" in an effort to stifle further gun-related tragedies.

Beauchemin And Anthony Are Apparently in A 'Situationship'

Beauchemin and Anthony's night on the town took place Wednesday this week at the Seasons Tickets bar in Manchester, NH.

A source told us the pair stayed at the pub for roughly an hour and a half, during which they knocked back a few cold ones and watched a Red Sox game.

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LONG TIME NO SEE

They apparently even showed a little bit of PDA during the date -- which didn't look like it was their first, either -- Anthony touched Beauchemin's arm and leg while they spent time together.

Another source told us the pair describe themselves as being in a "situationship" at the moment.

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NOTHING TO SEE HERE...

Anthony was spotted during a shopping trip at a T.J. Maxx following her night out with Beauchemin ... but he was nowhere to be seen.

'Love Island USA' Taylor & Clarke Say Huda Should Have Gone Home ... We Were More Genuine!!!

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HARDHEADED HUDA TO BLAME???

Taylor Williams and Clarke Carraway were voted off "Love Island USA" this week when America decided who their favorite couple is so far -- their pairing was dead last, so they got a one-way ticket home ... but they tell us their relationship wasn't given a fair chance!!!

If there's anyone they'd sacrifice for a spot back on the island, they'd throw Huda Mustafa and her connection with Chris Seeley overboard without hesitation -- saying their relationship is way more genuine than people know, and Huda's stubbornness ruined what she had going with Chris ... nothing new for our problematic queen.

Huda has been blasted with intense heat this season, online and from other islanders. Taylor and Clarke think there's no chance of her rekindling the connection with Chris, because she's stubbornly hard-headed.

casey anthony Mystery Man Revealed

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Casey Anthony's been spending time in New Hampshire with a local man who has led an interesting life ... and only TMZ found out who he is.

The bearded mystery man Casey was spotted cozying up to Wednesday night at a sports bar in Manchester, NH, is a man named Ben Beauchemin.

Ben owns a gun shop in Hookset, NH ... Wicked Weaponry ... and he's a war veteran and former Army ranger who enjoys skydiving. He also used to be a police officer.

Casey Anthony I Love A Good Deal At T.J. Maxx ... Shopping Spree After Date

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NOTHING TO SEE HERE...

Casey Anthony looks like she's settling into some new surroundings ... because after being spotted on a date in New Hampshire, she's doing some shopping nearby.

TMZ obtained video of Casey bolting out of the T.J. Maxx in Manchester on Thursday afternoon ... the day after she was spotted out on a date at a sports bar in town.

Casey's rolling solo on this occasion ...  and she's got two plastic shopping bags stuffed to the gills -- so it looks like she's stocking up on clothing and home goods.

Channing Tatum's Dating Life: From Jenna Dewan To Inka Williams!

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Channing Tatum's been through plenty of highs and lows over the course of his career ... especially when it comes to his love life.

The star of the "Magic Mike" franchise has been through a marriage, a divorce, and a subsequent engagement, the end of said engagement, and the beginning stages of a new relationship ... if that's not dynamic, we don't know what is!

Here's a look at how the actor's played the field and moved on from each one of his big splits.

Channing Met His Future Wife on Set

Tatum met his future wife, Jenna Dewan, on the set of the 2006 film "Step Up," in which they costarred -- and in case you were wondering, yeah, their characters ended up together.

The pair began dating, and the actor popped the big question after taking the actress on a romantic trip to Maui in 2008 ... and they didn't wait too long to tie the knot, as they held a wedding ceremony in Malibu the following year.

Tatum and Dewan announced in December 2012 they were expecting a child, and the actress gave birth to their daughter Everly the following May.

The two remained together for another five years before they revealed their separation to the public in April 2018, and Dewan formally filed for divorce the following month.

Although the pair were declared legally single in 2019, their divorce -- which Tatum described as "super scary and terrifying" at first during an interview with Vanity Fair -- wasn't finalized until September 2024.

Tatum Moved on From His Split ... With a Singer

Following his split from Dewan, Tatum dated around for a bit before he found himself with singer Jessie J, who he began seeing in late 2018.

A source spoke to Entertainment Tonight that October and claimed while the two had "just hit it off," the actor was "really" into the hitmaker.

After a year of PDA-filled outings and affectionate Instagram posts, however, the two split ... and a source told People in December 2019 that, while they were "still good friends," the actor and the singer had "different priorities and focuses that don’t really align."

But the pair were spotted in each other's company the following month, and four more months of loved-up snaps and videos on Instagram ensued.

Tatum and Jessie ultimately went their separate ways a second time in April 2020, and a source told People that, while the split was "totally amicable," both the actor and the singer realized that it was "better to move on" from their relationship.

Tatum Collaborated With His Future (Ex-) Fiancée

Tatum went back into work mode for a little while following his breakup with Jessie, and he was cast in a project that was eventually titled "Blink Twice" -- during which he met and worked with Zoe Kravitz.

Although the pair's relationship initially began on strictly professional terms, they eventually began being spotted in each other's company, and a source spoke to People in September of 2021 to express that the two had a "cute and flirty chemistry."

The performers remained together for another two years before it was announced that they got engaged in October of 2023.

While Tatum and Kravitz stayed engaged for a full year, they ultimately called off their plans to tie the knot in October of 2024, when they decided to end their relationship.

The actress opened up about her split from the "21 Jump Street" star in an interview with Elle, where she claimed that she still cared for her former fiancé "very much."

The Actor Ended Up Dating a Model

Tatum eventually dusted himself off and moved on from the end of his engagement, and he started being spotted with model Inka Williams.

We caught a video of the fashion industry personality keeping her arm around the actor while they attended a pre-Oscars party in February of 2025

An insider later told Us Weekly that, while the actor was "very interested in Inka," he was "trying to take it easy" during the early stages of their romance.

However, that didn't stop Williams from going Instagram official with the actor, as she shared a tribute to commemorate his birthday on her account in April.

Megan Thee Stallion Dating Klay Thompson ... Got a Splash Bro!!!

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Megan Thee Stallion's taking advantage of Klay Thompson's summer off-season ... the NBA legend was cryptically spotted in her new IG post -- and it's because they're dating!!!

The "Hiss" rapper has a win-win situation with her social media posts doubling as promo for her Hot Girl Summer swimwear line ... but Klay's "Where's Waldo"-esque cameo in the background of her poolside shot was hard to ignore!!!

Meg knows her way around the hardwood ... she was linked with Chicago Bulls player Torrey Craig up until her Coachella performance in April -- but seems like all plays are running through Klay now.

We reached out to Meg's team ... no word back yet, but given her Houston hometown and Klay's current slot with the Dallas Mavericks, seeing each other shouldn't be an issue!!!

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GET IT, MEG!!!

Jeremy Allen White's Relationships ... And His Family Life!

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Jeremy Allen White's become one of the buzziest actors of the past few years, and his starring role as Carmen "Carmy" Berzatto in "The Bear" has brought him an immense amount of press.

The thing is, not all of the attention is going toward his work as an actor ... a lot of it's being directed at the "Shameless" star's love life!

Here's a look at the performer's list of girlfriends ... and how he married one and started a family!

Jeremy's No Stranger To Dating Costars

White's been an actor for much of his life, and you gotta figure he's become familiar with on-set romances -- because he was in one!

The performer began dating his co-star Emma Greenwell, who joined the cast of "Shameless" during its second season, in 2011.

What's even wilder is that, in addition to their own relationship, the performers' characters -- Phillip "Lip" Gallagher and Mandy Milkovich -- were each other's love interest for a portion of the show's run ... how's that for life imitating art?

The pair's romance eventually ran its course, although they appeared to remain on good terms, as the actor showed up in a photo the actress shared on her Instagram account in 2014.

White Married -- And Separated From -- His High School Classmate

White subsequently began dating Addison Timlin, whom he met when he transferred to her high school in their hometown of New York City, and although she described their first encounter as "love at first sight" on the Showmance podcast, they stayed friends at first.

The pair, who also costarred in the 2008 film "Afterschool," eventually began dating, and they started a family when their first daughter, Ezer, was born in 2018.

White and Timlin tied the knot in a courthouse wedding ceremony the following year, and they added daughter Dolores to their family in 2020.

Although the actor remained together following the success of "The Bear's" first season, the performers ended up separating, and Timlin filed for divorce in 2023.

A source subsequently told People that, while the actress was "upset" about the end of her marriage, there was "still a lot of love between" her and White.

White Dated Around Following His Breakup

Following his split from Timlin, the actor was photographed making out with actress and model Ashley Moore during a steamy outing in Los Angeles in August 2023.

Although a source later told Us Weekly that the two were "totally smitten" and their chemistry was "off the charts," the actor's time with Moore proved to be short-lived.

White quickly moved on with Spanish singer Rosalia, first pictured together in October 2023, when they accompanied each other for a dinner date and screening.

The pair were spotted in each other's company during several subsequent PDA-filled date nights over the course of nearly a year.

Although it's unclear as to when White and Rosalia officially went their separate ways, they were last seen together in July of 2024.

White Quickly Moved On ... With Another Costar!

Remember that first costar that White dated? Turns out she wasn't going to be the last, as he was photographed locking lips with his castmate from "The Bear," Molly Gordon, in September of 2024.

Oh yeah, and life imitated art again with the actor -- his costar portrays his character's on-off love interest, Claire Dunlap!

A source spoke to People and claimed rumors on the set of "The Bear" began to swirl about the two while the show filmed its second season, and said the performers "had intense chemistry even when not filming."

They added White "really seems into Molly" and the two had become outwardly "affectionate" with each other.

While neither has directly spoken about their romance publicly, Gordon dished about the photos of her kissing White in an interview with Vanity Fair, and she chalked up the excited reactions of their fans to the byproduct of living in "a more judgmental society."

He's Also Had To Deal With Rumors About A Relationship With Yet Another Costar

White's also had to deal with plenty of rumors about the state of his friendship -- or relationship, as some fans have claimed -- with another costar from "The Bear," Ayo Edebiri.

The castmates have been spotted in each other's company on several occasions, and we actually caught them when they stepped out for dinner together on a night out in Beverly Hills.

The thing is, while neither White nor Edebiri have confirmed that they've ever dated, they've spoken fondly about each other as performers ... like when White told Vanity Fair he has a "tremendous amount of respect for" his castmate.

White also claimed there would be "no romantic implications" between Berzatto and Edebiri's character, Sydney Adamu, on the third season of "The Bear" during a press conference in 2024, Vanity Fair reported.

Casey Anthony Looking for Love?! Spotted Getting Cozy on Date Night

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Looks like Casey Anthony's got love on her brain ... 'cause she was spotted on what appears to be a date in New Hampshire Wednesday evening!

Check out the shots ... the formerly acquitted defendant appears to be in deep conversation with a bearded mystery man while dining at the Seasons Tickets bar in Manchester, NH.

Her tell-tale left shoulder tattoo is on full display -- remember, she had her controversial "La Bella Vita" ink covered up in 2018 and replaced with peonies and a half mandala.

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LONG TIME NO SEE

Harry Styles' Dating History: Actresses, Models And A Pop Star!

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Strap in, folks, because this one's gonna really stretch out for a while -- we're looking at Harry Styles' love life!

We all know the former One Direction member knows how to sing about the ups and downs of relationships, and he's written plenty of hits about that exact subject over the course of his career.

The thing is, some of his relationships have been just as dramatic and dynamic as his songs -- let's check them out!

Harry's Love Life Took Off With His Career

Styles was thrust into the public eye when One Direction was introduced through performances on "The X Factor" -- and he ended up briefly dating television presenter Caroline Flack, who had hosted its spinoff, "The Xtra Factor."

The pair received much attention for their 14-year age gap, and they ultimately went their separate ways after just a few months.

Styles was later linked to model Emma Ostilly, who appeared in the music video for One Direction's track "Gotta Be You," although their fling ultimately proved to be brief.

The performer subsequently started seeing Taylor Swift in 2012 ... and although they took several trips during that year's holiday season, they broke up in January 2013.

The "Watermelon Sugar" singer has spoken fondly of his ex in the years since their romance fizzled out, and he told Howard Stern the hitmaker was a "great songwriter."

Harry Got Used To Having High-Profile Girlfriends

Styles moved on with Kendall Jenner ... the couple was first spotted in each other's company while having dinner in West Hollywood in 2013.

Rumors about the pair -- who maintained what appeared to be an on-off fling -- swirled for several years, during which they were seen with each other on various outings.

Styles stayed busy in the interim, though, as he was linked to models Nadine Leopold and Georgia Fowler ... although neither fling lasted for very long.

The singer eventually reconciled with Jenner in 2016, and her sister Khloe told Entertainment Tonight that, while she didn't know if the two were "like boyfriend-girlfriend," the singer and the model "were in St. Barts together hanging out, so to me that's dating."

Although Styles and Jenner were later seen with each other during her 21st birthday party, their romance appeared to come to an end ... but they've stayed on friendly terms ever since then.

Harry Tried Playing Coy About His Love Life ... Until He Started Dating Olivia Wilde

Following his split from Jenner, the singer started seeing model Camille Rowe, and the fashion industry figure was photographed attending several of the performer's concerts throughout 2018.

The two attempted to keep their relationship under the radar during its length, and following their split that year, Styles included a voicemail from his ex at the end of his song "Cherry."

Styles then began the arguably most high-profile of his romances when he started dating Olivia Wilde, whom he met when he was cast in her 2020 film "Don't Worry Darling."

The singer and the actress -- who was formerly engaged to Jason Sudeikis -- first set off the rumor mill after they attended a wedding together in 2021, and they started being spotted together during his concerts, as well as on various getaways.

The pair, who had a 10-year age gap between them, garnered much attention for their romance over the remainder of 2021, and a line from Styles' track "As It Was" -- "leave America, two kids follow her" -- appeared to be a clear reference to their romance.

However, cracks between the two began to show over the course of 2022, and when their split was announced that November, a source told People the pair had come to a "very amicable decision" about ending their romance.

Harry's Since Embarked On Several Short-Term Romances

Styles eventually moved on with Emily Ratajkowski, and the two were snapped locking lips during a trip to Tokyo that took place in March of 2023.

Although a source told People at the time that the supermodel was "interested in seeing him again," the pair's fling proved to be brief.

Styles was later linked to actress Taylor Russell, with whom he was first seen in June 2023, and he attended the opening night of a stage production of "The Effect."

Their romance didn't last, however, and they went their separate ways by the following May.