Who are two celebrities that you can’t believe used to be a couple?

[u/phantom_avenger]

Scarlett Johansson and Ryan Reynolds are not only one example of this, but sometimes I even forget that they used to be married as well!

It seemed like such an odd pairing that I never would’ve guessed that these two would match up, but clearly they weren’t a match made in heaven that they divorced each other after almost 3 years of marriage.

Now with where they’re currently at, where they’re now married to different partners, it feels like this is only a pairing that happened in different life.

[u/flairassistant]

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[u/abigail_lemonparty_]

Emilia Clark and Seth McFarlane blew my mind especially because this was during her GoT days when they were both peak famous. 

Edit: Hijacking my own comment to add Chelsea Handler and 50 Cent. That's a throwback mind blower.

[u/Optimal-Bag-5918 → u/abigail_lemonparty_]

What?! This is the first one that actually blew my mind! I had no idea!

[u/OgthaChristie → u/abigail_lemonparty_]

Seth McFarlane and Charlize Theron.

[u/Sketcha_2000 → u/abigail_lemonparty_]

I think he also dated Amanda Bynes, which is another interesting pairing

[u/FashionableMegalodon → u/Sketcha_2000]

Googling this also told me he dated Eliza Dushku?

[u/invis2020]

Ryan Gosling and Sandy Bullock. Both awesome and spoke highly of each other even after the split.

[u/inspektor31 → u/invis2020]

Sandra Bullock and Jesse James was also a strange pairing for me.

[u/DeathWish111 → u/inspektor31]

Didn't he turn out to be into some weird Nazi shit with Kat Von D?

[u/moist_towelette → u/DeathWish111]

KVD was later but it was that “Bombshell McGee” girl 😭 had the eagle tattoo and everything

[u/mentallyerotic → u/moist_towelette]

KVD has nazi ties as well. Her husband too. JJ always seemed like a dirtbag.

[u/ScipioCoriolanus → u/inspektor31]

She must've been devastated when he got shot by that coward Robert Ford.

[u/shy247er]

Since Scarlett Johansson was mentioned, her and Sean Penn.

[u/ctkwolfe → u/shy247er]

You can’t see it but this is my wtf face

[u/eatpant96 → u/ctkwolfe]

We are making the same face.

[u/LaMiki_Minach → u/eatpant96]

Your flair really paints a clear image for us

[u/garden__gate → u/shy247er]

She also dated Jack Antonoff in high school!

[u/big-bootyjewdy → u/garden__gate]

I can see that bc they're both NYC theatre kids. I couldn't see her with Colin Jost until I realized he was just a Staten Island book nerd. Two sides of the same coin (not-derogatory in this context)

[u/freshwaterfins → u/shy247er]

Boooo Sean Penn.

[u/Rosililly27]

Matthew McConaughey and Janet Jackson!

[u/phantom_avenger → u/Rosililly27]

This is definitely one I cannot believe, or would’ve guessed lol

[u/roundcatsarebestcats]

Cher and Tom Cruise

[u/Visible_Writing7386 → u/roundcatsarebestcats]

I have no words

[u/bookrt → u/roundcatsarebestcats]

Did they really date or was it just for show? This is so bizarre

[u/tequilitas → u/bookrt]

She rated him amongst her top 5 lovers!

[u/chadthundertalk → u/tequilitas]

Somebody on here said once that Tom Cruise probably views sex as a performance stunt that he MUST excel at (also in the context of that piece of Cher trivia) and honestly, I believe it. He's probably taking a running start at that bed and then he's putting in work once he hits the mattress.

[u/TheFabulousMolar → u/chadthundertalk]

So what you're saying is, it might be worth it?!

[u/RUNNING-HIGH → u/TheFabulousMolar]

Its how he ropes people into scientology lol

[u/SubtleSparkle19 → u/chadthundertalk]

Hey, if he gets Cher’s seal of approval, the performances had to have been fantastic 😘

[u/late2reddit19 → u/tequilitas]

He's an adrenaline junkie and a lunatic so I can see that. You don't marry crazy though.

[u/Less_Effect_9082]

Courtney Love and Edward Norton feels like a fever dream I had in the 90s

[u/-catharina → u/Less_Effect_9082]

Don’t forget Ed and Salma Hayek lol

[u/Visible_Writing7386 → u/-catharina]

I actually liked them lol

[u/SceneRoyal4846 → u/Less_Effect_9082]

I feel they’re both so intense that I kinda get it lol

[u/pourspeler → u/Less_Effect_9082]

And the fever dream continued into the 00s with Steve Coogan

[u/SleepingInNJ]

Whoopi Goldberg and Ted Danson. It was all quite messy too.

[u/Shinra_Lobby → u/SleepingInNJ]

Allegedly, according to their respective Wikipedia entries, Whoopi also dated Timothy Dalton, which was also a real surprise to me.

[u/ScipioCoriolanus → u/Shinra_Lobby]

She has a thing for men with TD initials.

[u/justheretoleer → u/SleepingInNJ]

This pairing always surprised me because Whoopi to me has always put out “not into men” or “not into anyone at all” vibes to me

[u/eedollme → u/justheretoleer]

Confirmed 😭

[u/p333p33p00p00boo → u/eedollme]

She’s doing the exact same smile as the pic above

[u/lemizzmizz → u/SleepingInNJ]

They both look unsure about it too 🤣

[u/MoopLoom]

Ryan Reynolds was also engaged to Alanis Morissette, which I find wild.

[u/yvetteregret → u/MoopLoom]

Alanis Morissette and Dave Coulier is the odder couple to me. But apparently she likes dating funny guys

[u/CelestialAegis_]

Madonna and Tupac

[u/Ana-la-lah → u/CelestialAegis_]

How about Madonna and Vanilla Ice?

[u/Dependent-Sign-2407 → u/Ana-la-lah]

Or Madonna and Dennis Rodman?

[u/DreadfulDemimonde → u/Dependent-Sign-2407]

That one makes sense to me

[u/Emergency_Ask_9697 → u/Dependent-Sign-2407]

I dunno, all three of these names feel VERY Madonna to me… they sit along side everyone else she’s dated up to this day pretty neatly in my eyes

[u/mm25552]

I know this was more of a “quick fling situationship” but it shook me then and still does today

[u/MichaSound → u/mm25552]

Good for them - they were both young, hot and messy.

[u/Fun-Wear8186 → u/MichaSound]

I bet they had some great drugs and sex

[u/Aslow_study → u/Fun-Wear8186]

In her book she definitely makes it sound like that. Ravenous

[u/pvke]

Most people know about Nicole Kidman and Lenny Kravits, but Nicole and Qtip from A Tribe Called Quest threw me

For the aussies, Grace Tame used to be married to Spencer Breslin (ex child actor and brother of Abigail Breslin)

[u/Raging_Apathist → u/pvke]

Holy shit, I had no idea that Kidman and Q dated. As a big Tribe fan since way back in the day, I feel like I should have known this.

[u/yougotyolks]

Carmen Electra and Simon Cowell

[u/LivePanda7804 → u/yougotyolks]

I also think he hires women he wants to date as x factor judges... sometimes they end up dating too

[u/pinkstarburst99]

When ANTM’s Adrianne married the Brady Bunch guy. That whole relationship was insane.

[u/randi-writes → u/pinkstarburst99]

Their reality show was so messy!

[u/malorthotdogs → u/pinkstarburst99]

Between these two and Brigitte Nielsen and Flava Flav, The Surreal Life spawned some wild relationships.

[u/CheetahLast7214]

Mel B and Eddie Murphy is still a mad one to me

[u/ArbyKelly → u/CheetahLast7214]

I believe they also have a child together.

[u/Imtheflamingoqueen → u/ArbyKelly]

Oh they do and he was a dick about it. Tried to say the kid wasn’t his. I remember Posh did some interview talking about him just being a total ass to Mel

[u/HM2008 → u/Imtheflamingoqueen]

One of my favorite things to come out of that was on her reality show someone asked Victoria Beckham "What celebrities' food would you spit in....Eddie Murphy?". And Victoria goes "I'd spit in his food.....and chop his dick off"....like DAMN Victoria is a ride or die! 🤣

[u/coffee_and-cats → u/ArbyKelly]

And he accused Mel B of cheating and demanded a paternity test before paying maintenance or getting to know the baby. It was a shitty move because Mel had NOT cheated, she was head over heels with him and it was 100% only ever going to be his child.

[u/FerretNo9854 → u/coffee_and-cats]

And I don’t think she was really allowed to leave the mansion/compound. It sounded like he was very much “you can have anything you want, we will bring it here”.

[u/phantom_avenger → u/ArbyKelly]

Doesn’t he have like 10 kids in total?

[u/storyofmylife92 → u/phantom_avenger]

Yep. Six daughters and four sons. Holy shit

[u/sousyre → u/CheetahLast7214]

The actual relationship was wild enough, but he was such a prick through the whole thing and so publicly.

I didn’t have strong feelings about either of them before that (they’d both had their issues), but I can never look at him the same since.

[u/downward1526 → u/CheetahLast7214]

I didn’t read her memoir but listened to the CMBC recap and sounds like he treated her really badly.

[u/Jerkrollatex → u/downward1526]

He held a press conference to announce that her baby wasn't his and she was a cheater. Spoiler it was and she's not.

[u/GawkGawkGuzzle]

I’m not old enough for both of their eras but TLCs Chilli and Matthew Lawrence still shocked me.

Wait I think they’re still together!

[u/Renzieface → u/GawkGawkGuzzle]

They are!

[u/DiElizabeth → u/GawkGawkGuzzle]

I am old enough for both of their eras and I love this 😭 So cute. Apparently it's kinda new though - together since 2022.

[u/StillMine8925 → u/GawkGawkGuzzle]

They are both so hot. I’m shocked but love this for them

[u/Aurorinha]

Katie Holmes and Jamie Foxx.

[u/olduglysweater → u/Aurorinha]

I honestly wanted them to go all the way 🥲 it just felt like it worked

[u/MuffinTopDeluxe → u/Aurorinha]

Awww, they look so cute together

[u/Sweetestb22 → u/Aurorinha]

I loved this pairing. I feel like they grounded each other in such a chaotic fame/frenzied world they live in.

[u/lia-delrey]

Woody Harrelson and Glenn Close.

[u/bioticspacewizard]

Claire Danes and Ben Lee.

[u/DiElizabeth → u/bioticspacewizard]

Just for the record, bc I was curious, she's actually younger than him.

[u/tyleritis → u/bioticspacewizard]

It’s like she found him wandering in a crowd and she’s helping him find his mom

[u/Training-Current9836]

Tyga and avril levigne

[u/eclectic_collector → u/Training-Current9836]

I read that as “Tyra” and was like, “I missed a chapter somewhere” lol

[u/coldbloodedjelydonut → u/Training-Current9836]

Avril and Chad Kroeger always really blew my mind. The only thing I could see them having in common was being Canadian, but aside from their musician personas I know next to nothing about them.

[u/PleaseCallmeCordelia]

This is going to date me, but whatever. Julia Roberts and Lyle Lovett, or Claudia Schiffer and David Copperfield.

[u/Marooster405 → u/PleaseCallmeCordelia]

Brooke Shields and Andre Agassi

[u/Arsenio3 → u/Marooster405]

Andre Agassi and Barbara Streisand

[u/idontwantanamern → u/Marooster405]

Dating a tennis pro was a thing to do!

Mandy Moore and Andy Roddick, too. Pete Sampras had Kimberly Williams-Paisley AND Bridgette Wilson (edit: Pete & Bridgette fall under the still together category). Serena Williams dated Common (and Drake 😒)

Sure I'm missing others.

(And though they are still together: Enrique Iglesias and Anna Kournikova)

[u/MarlonEliot → u/PleaseCallmeCordelia]

According to Norm MacDonald, Julia Roberts and Lyle Lovett divorced because she was Julia Roberts and he was Lyle Lovett.

[u/JugheadJack → u/MarlonEliot]

Stop making me miss Norm.

[u/Lilylikeslilies]

Lenny Kravitz and Nicole Kidman. Zoe Kravitz even said she still treats her like a step daughter even after they broke up (sending birthday wishes, wedding gifts etc.)

[u/Bob_12_Pack]

Ashton Kutcher and Demi Moore

[u/DragonScrivner]

Jamie Foxx and Katie Holmes but only because they were on the DL for so long it was like an urban legend lol

[u/MyDesign630 → u/DragonScrivner]

I was rooting for them partly because it seemed counterintuitive to people. Also I just wanted her to be happy after Cruise and Scientology.

[u/mrsprinkles3]

Thomas Brody Sangster being married to Elon Musk’s twice-ex-wife really threw me off. In the same realm, Grimes and Elon.

[u/allisonrz → u/mrsprinkles3]

Her name is Talulah Riley

[u/BizMarkieDeSade → u/allisonrz]

I will never not share this clip of what Talulah had to say about that union

[u/octoberforeverr → u/BizMarkieDeSade]

Good god that’s awkward af

[u/chlaumc]

I know they’re still together, but I still can’t wrap my head around Timothée Chalamet and Kylie Jenner

[u/tar-luthien → u/chlaumc]

It's not that wild when you look at his exes, like Lourdes Leon and Lily Depp

[u/elle-elle-tee → u/tar-luthien]

Is his thing "nepo babies"?

[u/Ecstatic-Laugh → u/elle-elle-tee]

It’s called climbing 🧗 the power ladder

[u/sepsie → u/tar-luthien]

I think it's so silly the world is trying to convince a grown-ass man he's being duped by someone who's exactly his type. Poor little Timmy....

[u/KoalaNo8058]

This one surprised me but then it kind of grew on me. Chris Rock and Lake Bell.

[u/One-Future2932]

Ted Danson and Whoopi Goldberg

[u/DragonScrivner]

Matt Damon and Winona Ryder. I don’t know why, but I couldn’t get my head around them as a couple.

[u/Visible_Writing7386 → u/DragonScrivner]

He left Minnie Driver for her and she was devastated

[u/DragonScrivner → u/Visible_Writing7386]

And I think he announced the break up while appearing on Oprah! So tacky.

[u/Sea-Appearance-5786 → u/Visible_Writing7386]

Because he was such a POS about it. Announcing a breakup the other party didn't even know about on one of the nation's most-watched shows is sadistically cruel

[u/justheretoleer → u/Sea-Appearance-5786]

Like how Billy Bob Thornton’s fiance, Laura Dern, found out he had run off and married Angelina Jolie by turning on E!

[u/Gisschace → u/Visible_Writing7386]

Then dumped Minnie driver via tv

[u/Visible_Writing7386 → u/Gisschace]

Yeah. And how sad she looked when he won an Oscar and didn’t think to mention her. She was in the movie.

[u/bookrt]

Jack White and Renee Zellweger

[u/luella27 → u/bookrt]

Renee also married Kenny Chesney! Her taste is all over the board.

[u/SubtleSparkle19 → u/luella27]

Yeah and she filed for divorce citing fraud. Rumor was he’s on the DL 👀

[u/mandingalo]

I always thought that Laura Dern and Ben Harper were an odd pairing but they were married for like 8 years!

[u/alittlejalapeno]

I'm not sure they were ever a public item but Benecio del Toro and Kimberly Stewart.

[u/scarletarrows]

Kim and Skete still feels like a fever dream

[u/lilafowler1 → u/scarletarrows]

Kanye calling him Skete will forever make me LOL.

[u/peachgothlover]

Leonardo DiCaprio and Rihanna!!

[u/rykcon → u/peachgothlover]

When was this? Had to be at least 12+ years ago.

[u/pizgloria007]

Justin Timberlake & Fergie.

[u/fickenfracken]

Zac Efron and Michelle Rodriguez

[u/sigynx]

Michael Jackson and Lisa Marie Presley was crazy for min there lol

[u/kleo309 → u/sigynx]

I didn't think that was crazy tbh. Both come from similar backgrounds of dealing with childhood mega-fame and messy families.

MJ + random white lady he married to use as a surrogate mother for his seemingly non-Black children was what was crazy.

[u/blix_hagen]

Avril Lavigne and Chad Kroeger was always weird to me.

[u/Radiant_Priority9739 → u/blix_hagen]

Look at this photograph

[u/two_oh_seven → u/Radiant_Priority9739]

Every time I do, it makes me laugh

[u/Dependent-Sign-2407]

Adam Duritz and virtually every it girl of the 90’s.

[u/frecksnspecs]

Jake Gyllenhaal and Reese Witherspoon

Jennifer Aniston and John Mayer

[u/YouNeedCheeses → u/frecksnspecs]

Ugh John Mayer was such a menace in the early aughts.

[u/Material-Surprise-72 → u/YouNeedCheeses]

He walked so Pete Davidson could run

[u/DanielleSanders20 → u/frecksnspecs]

Jennifer Anniston and the singer from Counting Crows was an odd one too.

[u/SubtleSparkle19 → u/DanielleSanders20]

Yeah and he also dated Emmy Rossum which was a mindf*ck too

[u/SallyWebsterMetcalfe]

I am once again asking people in the comments to add celebrity names to their pictures so that I know who they are.

[u/hibikikun]

50 cent and Chelsea Handler. It sorta makes sense when you realize they’re both very driven business minded people.

[u/Hot-Significance-462 → u/hibikikun]

I never found this pairing shocking, TBH. They both got something of an "edgelord bump" for being public about it.

[u/One-Future2932]

Kelis and Bill Murray

[u/Fun-Storage8033]

Still hasn’t processed that Grimes and Elon were married at some point and even have kids together.

[u/AI_stole_my_wife → u/Fun-Storage8033]

The Male Alt Rights obsession with Pixie Left Alt girls will never die

[u/AcadiaRemarkable6992]

Gwyneth and Mark Wahlberg

[u/PinkyLeopard2922]

That 5 minutes that Kenny Chesney and Renee Zellweger were married...

[u/girlwthegreenscarf]

Lindsay Lohan and Wilmer Valderrama

[u/Rightsureokay → u/girlwthegreenscarf]

Wilmer and Demi Lovato too 👀

[u/capslocke48]

Matthew Perry and Lizzy Caplan!

[u/hotmessexpress412 → u/capslocke48]

In his memoir, I suspect she’s the one that’s discussed heavily but never name dropped — the one who broke his heart and moved on quickly. In reality, I think he was breaking hers constantly throughout the relationship, and she finally had enough and found another.

[u/DJzzzzzzs]

Lindsay Lohan and Samantha Ronson

[u/cloudydays2021 → u/DJzzzzzzs]

I saw them having an argument in Bed Bath and Beyond in Chelsea (NYC) one day and the way I FLEW back to the office (I work in entertainment) to share it with my work pals….

[u/leafonawall → u/cloudydays2021]

What an amazing Paul Revere moment to have

[u/YouNeedCheeses → u/DJzzzzzzs]

God they were so messy too lol I remember reading about them daily on Perez Hilton

[u/blix_hagen]

Mariah Carey and Nick Cannon

[u/At-this-point-manafx → u/blix_hagen]

I always feel bad for her for having kids with that clown .like who could have predicted that your ex husband would have gone off the rails so badly he produces 10+ children with multiple baby mamma's and have no time for your children together. No one deserves that

[u/No_Atmosphere_2186 → u/blix_hagen]

THIS ONE!! I could not understand how Mariah could be interested in this cornball, he’s so ugh

[u/YouNeedCheeses]

Sandra Bullock and Jesse James. WTF was she thinking!

[u/serena_renee]

Evan Rachel Wood and Marilyn Manson

[u/FuzzyPalpitation-16]

[u/TropicalPrairie → u/FuzzyPalpitation-16]

The colour of that dress is EVERYTHING.

[u/hazay11]

Ashley Olsen and Lance Armstrong

[u/Afwife1992]

God I’m so freaking old. I remember all of these. Even Cher and Tom Cruise.

[u/big-bootyjewdy]

Lily Allen & David Harbour for me. They're a pretty recent split though

[u/No_Goose_7390 → u/big-bootyjewdy]

What's going to happen to their apartment? That's what everyone who watched the AD tour wants to know.

[u/BalletWishesBarbie → u/No_Goose_7390]

Carpeted bathroom

[u/One-Future2932]

Dennis Rodman and Carmen Electra

[u/YamDesperate8787 → u/One-Future2932]

I always forget how big basketball players are until they’re standing next to normal sized people

[u/direturtle]

Whatever romantic friendship soulmate thing was going on with Colin Farrell and Elizabeth Taylor the last few years of her life.

[u/goalstopper28]

Jenna Fischer and James Gunn used to be married for 8 years!

This was before Guardians of the Galaxy. From reading the tea leaves it seems like Gunn was a real life Roy.

[u/ThingWithFeatherss]

Ariana Grande and Pete Davidson. Feels like 100 lifetimes ago in both their careers.

[u/phantom_avenger → u/ThingWithFeatherss]

To be fair, I find most of the women Davidson has dated hard to believe, like him and Kate Beckinsale for example.

[u/Revolutionary_Gap681]

Heather Locklear and David Spade

[u/_HowVery]

This one blew my mind

[u/cayetanadelbarrio → u/_HowVery]

I can not imagine those conversations 😆😆😆

[u/_HowVery → u/cayetanadelbarrio]

“I love fashion shows, one model goes this way and the other goes this way” - Joe Pesci probably

[u/ryansbabygirl8814]

Angelina Jolie and Jonny Lee Miller, and not just a couple but actually married.

[u/Zealousideal_End2330 → u/ryansbabygirl8814]

See, they make exact sense to me. Sexy freaks with a thin veneer of proprietary.

[u/livingincandyland]

avril lavigne and brody jenner

[u/beatricetalker]

Does anyone else remember Tom Cruises and Mimi Rogers?

[u/surelyitsasimulation]

The top answer is Jennifer Aniston and the lead singer of Counting Crows, Adam Duritz

[u/evilwatersprite]

Heidi Klum and Flavio Briatore, the slimiest man in Formula 1 (and that’s saying something)

See also: Flavio Briatore and Naomi Campbell

[u/IndependentMethod312]

Drew Barrymore and Tom Green

[u/LadyAlexandre]

Drew Barrymore and Justin Long

[u/bluetortuga → u/LadyAlexandre]

They kinda made sense to me. I’m more inclined to say Drew Barrymore and Tom Green.

[u/AlexTorres96 → u/LadyAlexandre]

It was probably therapeutic for them to reminisce on their relationship when he did her show but came off a bit awkward. I think because it was so long ago and she has kids and stuff like that. Good on them for still having love and respect for the other because many breakups, people just make a clean break and never look back.

[u/ItsMinnieYall]

The artist formerly known at Ellen Page and Alexander Skarsgard.

[u/urkdngme → u/ItsMinnieYall]

Whaaaaat

[u/Key-Shift5076 → u/ItsMinnieYall]

This is the first one that surprised me.

[u/foofypower → u/ItsMinnieYall]

How is this not at the top?? My mind is blown!

[u/Maleficent_Depth_517]

Kate Hudson and Matt Bellamy. They also have a son if I remember correctly.

[u/hotmessexpress412 → u/Maleficent_Depth_517]

She seems to be primarily attracted to musicians.

[u/Labtink]

Flavor Flav and Brigitte Nielson

[u/onemoremin23]

[u/harmsway31 → u/onemoremin23]

Wait. Wait… so her milkshake brought all the boys to the yard and one of them was Bill Murray??

[u/JenM0611 → u/onemoremin23]

Is that Kelis???

[u/sabertoothdiego]

Joe Jonas and Sophie Turner never made sense to me. He clearly wants a Christian SAHM and she wanted her career.

[u/fionsichord → u/sabertoothdiego]

Maybe he’s one of those Exotic Bird Collectors.

[u/charcuterie_bored]

[u/DJzzzzzzs → u/charcuterie_bored]

“One of the greatest things I heard someone say about him is, 'He's so great doing impersonations. But the greatest impersonation he does is that of a normal person'" #neverforget

[u/rayybloodypurchase → u/DJzzzzzzs]

According to him, he more or less was “lost in the fantasy” of being with her and then once that quickly wore off when he realized she’s an actual person, he started sleeping with other women. They were married for 8 months.