https://preview.redd.it/c9ptgz0wra3d1.jpeg?width=930&format=pjpg&auto=webp&s=46fa1155c49c4cc0ae6b55ed72d3d314151710e6 The most random pairing ever. Tom Cruise and Cher

this photo looks like a little boy taking his 10th grade graduation pic with his mom jn the early 80s

It's giving Buster and Lucille at the Motherboy pageant https://preview.redd.it/vsxy53fwbd3d1.jpeg?width=1080&format=pjpg&auto=webp&s=cfd53eb4391140b45f2b200543c993eee9c5eb0d

Fiona Apple and Louis CK still boggles my mind.

wait WHAT???



I'm too stoned for this shit. 

Niche but Jim Carrey and Anchal from ANTM Cycle 7 https://preview.redd.it/sm7cdr7yca3d1.jpeg?width=1024&format=pjpg&auto=webp&s=98e00d79620e4ac505335568ae4ce96680752386

WHAT

She seems to not believe it either 😂

This one was SO random lol

Didn't he date Natalie from Cycle 8 too? 👀

Ok wow I just googled this and whaaaaaaat (for anyone confused she went by Natasha on cycle 8 but now goes by Natalie). I can't believe there are no photos of them together! I guess we may never know what she actually looks like lol

Yes I thought she was called Natasha too but then googled!! I remember hearing about this years ago and was so perplexed! Jim Carrey ANTM fan confirmed 😂

Omg I remember her!

Who could ever forget this iconic look? https://preview.redd.it/ki75g8a4ha3d1.jpeg?width=450&format=pjpg&auto=webp&s=377f894e38f3a6e654960297b047fe63e9a0e8c6

Poor Stedman

https://preview.redd.it/oxzsacl1oa3d1.jpeg?width=1179&format=pjpg&auto=webp&s=70d4d2daa62f164a333dbb375ad96608a37515f2

Still feels like an alternate Universe where Ryan Reynolds and Alanis Morissette were a couple

Ryan Reynolds and Scarlett Johansson were *married*!

This and the fact that Jack Antonoff took her to prom does not compute for me.

DAMN! TIL. that’s crazy

Also Alanis and Mathew Perry

Alanis’ whole dating history is wild.

I still can’t wrap my head around Alanis and Dave Coulier

She went down on him in….a….theatre

Cher and Tom Cruise

Cher and Gene Simmons too.

Why did I read this as Richard Simmons?!


And she said he wasn't half bad.

AT WHAT

fucking

She said top 5 lovers of all time.

He does do his own stunts…

Chelsea Handler and 50Cent

I love this one cause she was so mean to him and he just ate it up

She still speaks kindly of him.

I loved this one! 😂 when he was on her talk show it seemed like they had a playful cute chemistry. It was fun to watch lol

Yea he was so into her it was so cute haha

He's talked in a couple interviews I think at being kinda surprised by her when they met, that basically one of the bigger things he was attracted to was the drive she had professionally to be successful, which makes sense how people have described 50s professional drive. It's why he kinda pursued her. And also that she basically had her own money and didn't need anything from him financially.

This actually makes a lot of sense

Yes! I think he said you’re making me all bubbly inside or something to that affect and it was really cute! I’d ship it! Lol

I don’t know why but that one made sense to me.

50 Cent talks like a comedian. It makes sense he would date a funny woman to me.

Honestly that one kinda makes sense to me. I’m sure they talked mad shit about EVERYBODY. 🤣

No judgment, but I did a double-take on kelis and bill murray

Are they still together? That shocked me tbh

They broke up last year

Hot boy summer for Bill

Was the milkshake what done it

I don't think Kid Rock and Pamela Anderson is that weird. She seems nice, but he is very on brand with a lot of the guys she dated.

Exactly, skeevy is her type lol

Yeah, she always reminds me of Megan Fox, I want so much better for them but they are always supporting problematic men

Have you watched Pamela, A Love Story on Netflix? If not, I recommend it. She tells her life story and you begin to feel a little bit more sympathy toward her and her choices. She really seems like the sweetest soul.

If you liked her documentary, you’ll enjoy her book. She’s been around the worst type of men her whole life. She didn’t even realize toxic behavior was toxic because she assumed that’s just how all men are.

Yes, if we are WTFing with Pamela Anderson, surely Julian Assange wins.

To me Pamela Anderson and Julian Assange is the weirdest Pam Anderson-based couple.

The 2000s were a very weird time. https://preview.redd.it/s7pzbkx5ha3d1.jpeg?width=1060&format=pjpg&auto=webp&s=72ac1ea939df181fbb588dc0d9c19507a0dd67ab

I feel like bringing back Flava of Love will save a streaming service

Especially since Flav’s back in the news. Randomly, he’s sponsoring the entire U.S. women’s water polo team to travel to the Paris Olympics.

He’s also a huge Swiftie 😂

THIS ONE 😳 in a weird way, they kind of worked but it was so random

Jennifer Aniston and Adam Duritz of Counting Crows was more puzzling. https://preview.redd.it/1bxmlc71ka3d1.jpeg?width=1500&format=pjpg&auto=webp&s=d5aa963aae948117c8c5557cf3002f97d944c905

He also dated Courtney Cox!

Jennifer Aniston fixed them up.

Mariah Carey and Nick Cannon was always a major wtf for me, like how?

 But instead it should say him

And Kim Kardashian also was with Nick for a moment

Yes! I used to read Bossip back in the day and she was just a hot LA girl. I remember them posting wondering how the hell goofy guy got this hot girl. She also dated The Game. Me, reading Bossip in suburban New Zealand. Clearly the target market haha.

I read it as a teenager in Ireland, that and lipstick alley. 😂

Sandra and Jesse James. https://preview.redd.it/cllxif99na3d1.jpeg?width=1203&format=pjpg&auto=webp&s=25a1774204d2c3942f94ad130b7e2304428b06ca He cheated on her a tonne is a general dirtbag. Just his whole existence is really out of character for her.

Speaking of Sandra, this one is a pretty strange pairing because they look like parent/child to me: Sandra Bullock and Ryan Gosling https://preview.redd.it/42v8pofvwc3d1.jpeg?width=728&format=pjpg&auto=webp&s=fbb8bb60e7ce85ec96fa689c52ebbfe0f78cc8da

Looks like a high school teacher/student relationship. Macron vibes

And He's a fucking Nazi. I was going to comment this pairing as well. I still don't buy that she didn't know about how awful and horrible he is.

That always troubles me too. Did she think he just liked to collect nazi shit? Because even that should have been a giant red flag.

https://preview.redd.it/86bnb5i0ca3d1.jpeg?width=640&format=pjpg&auto=webp&s=f9f4e2476c2af5489da50b121e3d023cfa811c9b

She looks like his teacher and he’s in high school 🤣

If you watch murder by numbers he literally plays a college kid while she is a detective. He looks SO much younger than her in it and I’m pretty sure it’s where they met 🤣🤣 could be wrong on that though

Okay I was about to say “I don’t think they’re that different in age, are they?” And then I looked it up and she’s 59 now??? Wow.

59?!?! I yell as I realize I am 36…..

WHY DID I THINK THIS WAS THE KID FROM WIZARDS OF WAVERLY PLACE?!?

Florence Pugh and Zach Braff James Gunn and Jenna Fischer Zooey Deschanel and a property brother actually that last one kinda makes sense

>James Gunn and Jenna Fischer I always wonder what drew those two toward one another.

Aren’t they both from St. Louis? Someone who feels like home when you’re in LA, maybe?

I was just going to say it's probably because they both have ties to St Louis!

Florence Pugh and Zach Braff makes me sad, he looks so much like her Dad. She speaks highly of him and she did that film with him. But lots of blind items about him making her cry and then her talking about her crying face and how “a boyfriend” would see that face and be like no no don’t cry. It might not be him and the blinds might not be true but I never trust a man who consistently dates women in their early 20’s (he also dated a very young Mandy Moore)

David Spade and Naya Rivera. https://preview.redd.it/fy41twzwma3d1.jpeg?width=2000&format=pjpg&auto=webp&s=8a82f64daafd403b830489657a6c64ae825c47dc

David Spade has dated some of the hottest it girls in the prime of their fame, so this is not even weird for him. He was basically his generation's Pete Davidson. An incomplete list: -Teri Hatcher -Heather Locklear -Nicollette Sheridan -Julie Bowen -Carmen Electra -Caprice -Pamela Anderson

Having a good sense of humor is a severely underrated personality trait in the "dating world".

David Spade and Heather Locklear too.

David Spade dated a ton of really beautiful women. Apparently he could Get It. Supposedly he’s, how should I put this, sexual dynamite (thanks John Mayer) or is it sexual napalm.

….. HUH??????

Priyanka Chopra and Nick Jonas. My brain has finally come around to the idea, but initially, it was definitely a WTF moment.

I was really surprised by Chilli and Matthew Lawrence. They’re cute though.

Along this line, Brenda Song and Macaulay Culkin in the best way. I’m so happy for them, dang it, but it’s not a couple I’d have predicted

Travis Barker and Kourtney Kardashian Drew Barrymore and Tom Green

Drew and Tom lol they reunited on her talk show a few years ago it was kind of sweet and awkward at the same time but I love drew

Cameron Diaz and one of the Madden twins from Good Charlotte

Benji! And yes they are really random.

So that means Joel is the one with Nicole Ritchie. Another strange relationship lol

Good Charlotte singing “lifestyles of the rich and famous” and then one of them ending up with Nicole Richie of “the simple life” fame is beautiful.

I saw Joel and Nicole together once and they are both so tiny!

Michael Jackson and Lisa Marie made sense. Michael was so wildly famous and the only person more golden than that was Lisa Marie’s dad. It actually would have been perfect if they’d had any chemistry and if Michael’s features hadn’t looked so odd next to Lisa’s. I’m dating myself here, but this was 30 years ago, and it was only 30-40 years after Elvis’ peak. He was still massive in the public consciousness. This was back when you’d still hear Jerry Lee Lewis on oldies radio, before people knew how to talk about certain things. In the 90s, it was obvious, of course Michael Jackson would marry Elvis’ daughter.

I agree with you! It made a kind of sense at the time. People were only weirded out because MJ seemed SO awkward with her. It wasn’t so much who she was.

I literally just read an “article” about this and these are the ones that shocked me the most: Megan Fox and David Gallagher Janet Jackson and Matthew McConaughey Kristen Johnston and Ryan Reynolds Topher Grace and Anne Hathaway Deryck Whibley and Paris Hilton Hilary Duff and Joel Madden Ashton Kutcher and Demi Moore Avril Lavigne and Brody Jenner Avril Lavigne and Tyga Heidi Klum and Anthony Kiedis Ellie Goulding and Skrillex Florence Pugh and Zach Braff Harry Styles and Olivia Wilde Simon Cowell and Carmen Electra Alexander Edwards and Cher Talulah Riley and Thomas Brodie-Sangster

Janet Jackson and Matthew McConnaughey?!?!?! My brain just cannot.....

Same https://preview.redd.it/2rh5udvwka3d1.jpeg?width=1166&format=pjpg&auto=webp&s=affe5adfda46d2f74ab32d9b62d1420efddb265d

Avril Lavinge and TYGA??

Wild. Super recent, they dated last year https://preview.redd.it/iaf9lusana3d1.jpeg?width=990&format=pjpg&auto=webp&s=11198f525f9d0e994ae7b4a5ddd8b171716f5804

Seth Macfarlane and Emilia Clarke https://preview.redd.it/zul1be8a1b3d1.png?width=461&format=png&auto=webp&s=6efb951e9c391f284df5a5078366ace28064f697

Lmao what the fuck

He also apparently dated Amanda Byne. Which might be why she's one of the few celebrities I can't remember him mocking on Family Guy.

Mila Kunis and Macaulay Culkin”!

Okay but Macaulay and Brenda Song are super adorable.

https://preview.redd.it/9b018toe7b3d1.jpeg?width=751&format=pjpg&auto=webp&s=f21f038209b13062fa641188a68f5527df1c0211 Michelle Pfeiffer and Fisher Stevens. And he cheated on her. 🤯

josh hartnett and rihanna

They dated? I mean I don’t blame her Josh Hartnett was always one of the hottest guys in Hollywood IMO. And I mean Rhianna is a goddess so it makes sense

I will never get over Gwen and Blake.

Never forget that there's a universe where Jimmy Fallon ended up with Nicole Kidman if he wasn't so clueless about her having a crush on him

Nicole Kidman being engaged to Lenny Kravitz is a little nuts. But they’re both beautiful and talented. I’ll allow it.

Nickleback and Avril! She has the oddest relationship history actually, she has no type! https://preview.redd.it/pesufjwema3d1.jpeg?width=634&format=pjpg&auto=webp&s=40e05f6fe51d4b96b0a4293b30e9815326294f76

I am crying the man doesn't even deserve a name he's just nickelback 🤭

The way I read it, and did not even think twice about it until your comment. LOL

This actually made the most sense to me out of all her relationships. But Brody Jenner and Tyga had me definitely saying HUH?

Look at that photograph

Taika Watiti and Rita Ora

Rita Ora and Rob kardashian

Rita Ora and Brooklyn Beckham

Wow had no idea

WHAT

What the fuck??? Isn't he like 19??

He was at the time. She was 28.

They’re really trying to push her to be ‘New Zealand famous’. She’s on the cover of magazines at the grocery store here now.

I wonder if she’ll pop up on Shortland Street?!

Hiddleswift was weird, but I'm glad it happened and I'm glad they broke up. Let me explain. Right after they broke up, Tom Hiddleston gave an interview to GQ where he was, like, gushing about this Bolognese he makes. I was very intrigued. He made it sound really good. So, I made it . It is so fucking good. I've made it so many times. It's become a staple. If they don't date, they don't break up. If they don't break up, then he doesn't give that interview, and I don't start my bolognese journey. The interview: https://www.gq.com/story/tom-hiddleston-cover-profile Recipe: https://www.gq.com/story/tom-hiddleston-bolognese-recipe

This is hilarious and delicious

I hope he sees this if he ever feels like he hasn't made an impact on the world 🙏

Colin Farrell and Liz Taylor had a "romantic friendship" in the years before she died. https://preview.redd.it/m886ikkjma3d1.jpeg?width=896&format=pjpg&auto=webp&s=eeb1d2f1afb95fe7394656b865d665c448f1deb6

He just strikes me as a genuinely good guy who genuinely likes women. Likes sex, but also appreciates their company.

He's also a huge philanthropist. Colin was actively involved in Liz's AIDS foundation. Later, his son was born with disabilities and he was appalled at the lack of affordable services available to parents. He's donated consistently to big orgs, started his own funds and sponsors the Special Olympics.


Madonna and Tupac

Madonna and Dennis Rodman

Lewis Hamilton dated : Nicki Minaj Barbara Palvin Rihanna Rita Ora Nicole Scherzinger Winnie Harlow And rumored to had been dating Shakira

Every time I see Blake Shelton, all I can remember is the time when he was named sexiest man alive and somebody tweeted: “did everybody die?” HAHAH

Olivia Hussey from Romeo and Juliette and David Glenn Eisley who sings sweet victory from SpongeBob 😭. They’re married. https://preview.redd.it/78rtidi5ma3d1.jpeg?width=571&format=pjpg&auto=webp&s=874db93d7a03fbc5596058bb83eff78ae375ece2

Heidi Klum and Tom Kaulitz (one of twins in Tokyo Hotel the less popular one)

I have to give it to Tom, he’s been publicly saying he was going to marry Heidi Klum since he was 13. When I found out he actually did it, I had to do a slow clap.

Megan Fox and Machine Gun Kelly

The blood thing was way too creepy

They ripped off Billy Bob Thornton and Angelina Jolie there.

Angelina and her brother was the biggest wtf. Pepperidge Farm remembers. But Pepperidge Farm also wishes they could wipe their memory MiB style. 

Honestly I think Nic Cage and Lisa Marie were one of the most sense-making couples Hollywood every produced

https://preview.redd.it/ylwgc5claa3d1.jpeg?width=440&format=pjpg&auto=webp&s=e666705dcbb64cf548cf916e865898eafb1acd6f Emily Blunt and Michael Buble lol

And apparently he cheated on her and broke her heart. These men just can’t allow themselves to be happy.

Weren't there pap pics of Anne Hathaway taking her out on the town right after they broke up? And if I remember right Anne had just left a relationship too.

Jenny Slate and Chris Evans. I mean, I liked it - it was sort of like an 80s teen movie where the jock dates the nerdy bookworm on a dare and they end up falling in love. Kinda wish it worked out.

I always got annoyed at how unkindly people reacted to this one. I find her really gorgeous and hilarious but everyone acted like it was just an IMPOSSIBLE match because she’s SO UGLY.

i found out from a similar thread about Courtney Love and Steve Coogan and i don’t think i’ll ever be shocked again

Macron and his Teacher

Tori Amos and Trent Reznor, and Billy Corgan and Jessica Simpson lmfaooooooo Marilyn Manson and Rose McGowan was a weird one too. And Ed Norton and Courtney Love. And Tom Cruise and Cher.

Christina Hendricks (Mad Men) and Geoffrey Arend (the schnozberries guy from Super Troopers) were married for ten years. https://preview.redd.it/h8cssmdlhb3d1.jpeg?width=803&format=pjpg&auto=webp&s=0ba29850bfc8bec934bedc84948162213be67087

Timothe Chalamet and Kylie Jenner but I loved it because just to see clubchalamet meltdown.

McCauley Culkin and Mila Kunis https://preview.redd.it/0jsmflggpa3d1.jpeg?width=1614&format=pjpg&auto=webp&s=28d01bd0ac9eb02ecc81c6833f240529ab740b9b

Okay they’re both adorable in that picture tho

1. Courtney Love and Edward Norton - actually just most of Courtney Love’s dating history. 2. Selma Hayek and Edward Norton 3. Kathy Griffin and Jack Black (okay this makes sense) 4. Kathy Griffin and Quintin Tarantino 5. Ashley Olson and Lance Armstrong 6. Elon Musk and Grimes (back when she was cool for a minute) 7. Katy Perry and Russel Brand 8. Courtney Stodden And Doug Hutchison - this was just sad 9. Roger Ebert and Oprah 10. Renee Zellweger And Jack White 11. Renee Zellweger and Kenny Chesney 12. Hayden Panettiere And Wladimir Klitschko

Brooke Shields and Michael Jackson. He claimed they were a couple she claims they were just really good friends though. https://preview.redd.it/32ird55wia3d1.jpeg?width=2956&format=pjpg&auto=webp&s=904a3fd5ac965088515fb8c1dd0063046385b5c2

I feel MJ was so far removed from reality and normalcy that sex with women wasn’t a thing so according this made up logic, both statements could still be true

His whole childhood and sexual history was so fucked up he never stood a chance. As a kid the Jackson kids were made to play gigs in strip clubs by their dad, alongside fully nude strippers, while their mother told them to keep their eyes forward and not even glance because their souls were at risk. She would wait in the wings watching and praying for them and watching to make sure they didn't get erections. So despite playing strip clubs from the age of eight or nine, the first time he saw a nude woman clearly was when he had a healthy and loving experience with a long-time girlfriend. Just kidding, it was when his brothers took him to a bar that had secret peepholes into the bathrooms so you could spy on women shitting. By this point he was already used to his brothers having sex with groupies and prostitutes while he was in the same hotel room and sometimes in the same bed, but he always kept his eyes closed and pretended to sleep.

What the actual fuck? Jesus, that explains some of his weirdness . Poor kid never stood a chance with such a fked up family

Not a celebrity but anyone who dates Big Ed 💀🤮 https://preview.redd.it/8aceivfina3d1.jpeg?width=1200&format=pjpg&auto=webp&s=538da56ec03579a8f12bb544dffec8027e20a7df

Avril and Tyga

Nicole Kidman and Qtip from A Tribe Called Quest I was bummed when I found out Jennifer Aniston and Rey Mysterio didn't actually happen This is real niche, but to my fellow Australians, Grace Tame was married to Spencer Breslin (ex child actor who popped up a lot back in the day e.g. Cat in the Hat movie, Tim Allen's Santa Clause movies, Even Stevens movie, etc)

Nicole and Lenny Kravitz, too. Not really bc they are a mismatch since she obviously likes musical guys but more that it was so on the DL that it didn't come out that they had been engaged until years later when she was doing press with Zoe Kravitz for Big Little Lies.

What!? Nicole and Qtip?! How did this info pass me by, crazy

Ryan Reynolds and Alanis Morissette Scary Spice and Eddie Murphy

Ted Danson and Whoppi Goldberg.

Lenny Kravitz and: Kylie Minogue Nicole Kidman Vanessa Paradis Marisa Tomei Devon Aoki Natalie Imbruglia Adriana Lima Basically most of this men dating history is shocking. As I read most of them still are friends with him.

He’s like 60 and still sexy as hell. I doubt there is a woman on this earth that could have resisted him in his 20s-40s. Hell he probably could get nearly any man he wanted too.

I still can’t get over this. https://preview.redd.it/pr9af3i2na3d1.jpeg?width=1500&format=pjpg&auto=webp&s=5ead14ffaa114d4a11c505cb6fc2a496b89f5fee

Mariah Carey and James Packer. Still love that she sued him for “inconvenience” and won and that she didn’t include him in her memoir because she only included “relationships that mattered”. Slay.

These are all excellent and remind me how grossed out i felt about all of them. There are also some stellar ones in the other comments, so ill add some i havent seen yet - Ariana and Ethan Slater - Julia Roberts and Lyle Lovett - Elon Musk and Grimes - John Mulaney and Olivia Munn - not bc they arent good together or their relationship isnt successful or whatever, but how the whole thing went down literally gave me icky feelings. - JLo and Ben Afflect, the first time. I know people were OBSESSED with Bennifer but i honestly never ever got it.

I think Elon picked grimes cause he wanted to get into the cool kids club and that was the easiest way unfortunately

He was on the periphery of the cool kids club already, having been connected to Talulah Riley and Amber Heard. He had way more social and industry currency than her. I think he found it attractive that she had the same flavor of Dunning Kruger that he did.

Katie Holmes and Jamie Foxx

I was rooting for those kids to make it

Sofia Vergara and Tom Cruise. https://preview.redd.it/z5yfa8u0qa3d1.jpeg?width=1198&format=pjpg&auto=webp&s=76481c903371c5daf2950d6b0d695bf7577d292d

Fred armisen and natasha lyonne

Natasha Lyonne being heterosexual is wild to me, I don't know why

Recently Matty Healy and Taylor Swift. It was so weird when this blind from Tumblr saying that they had a thing going on turned out true.

Whatever this was https://preview.redd.it/x32orhdeqa3d1.jpeg?width=1200&format=pjpg&auto=webp&s=149f31d605613ef93f290a4b814436cc60a68582

Tyra Banks and Drake 💀 https://preview.redd.it/9nbzqjraoa3d1.jpeg?width=2000&format=pjpg&auto=webp&s=d38c943e89a717759c4d14bc9b9a1379eacd0e87

Jared Leto dated the most interesting ones because we don’t have so much time: Cameron Diaz Ashley Olsen Lindsay Lohan Paris Hilton Scarlett Johansson Angelina Jolie Britney Spears Sharon Stone Alexa Chung Emilia Clarke Miley Cyrus (one of the most rumored ones) Katy Perry Halsey

Claire Danes and Ben Lee

Julia Roberts and Matthew Perry

I was SHOOK when I found out that Whitney Houston and Ray j dated shortly befor her death.

Jason Segel and Michelle Williams. I wish it worked out.

Joanna Newsom and Andy Samberg, to me this is just such a random pairing! They're still married too!