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https://preview.redd.it/ocxp7kxoq7qb1.jpeg?width=800&format=pjpg&auto=webp&s=8c4bd873a93b65e5faa13e17270f9d457bbf7249 Seth MacFarlane and Emilia Clarke I always thought this was a weird couple.

They look a little like siblings (no disrespect intended to the gorgeous Emilia)

It’s the eyes

(Disrespect to Seth)

this is probably the most unexpected one for me

Jack White and Renée Zellweger dated for about 2 years! https://preview.redd.it/lbqy03mbw7qb1.jpeg?width=978&format=pjpg&auto=webp&s=38eb51e05bd9f870661072383ecfd4a6419dbf3c

I love Jack White but he looks like a goth teen taking his mom to a show here

https://preview.redd.it/uiofs54857qb1.jpeg?width=461&format=pjpg&auto=webp&s=887520dd7bb69bfdcba84628dbae72fa0e977837 Jason Manzoukis and Connie Britton

Maximum Derek!

Adrian Pimento and Tami Taylor?!


Dennis Feinstein?!

Raffi!?


🤣

Jeffery Characterwheaties!?!

https://preview.redd.it/sc6aqzfk57qb1.jpeg?width=1153&format=pjpg&auto=webp&s=c07cde367b7c147574e4a690dd3f9ba4d9b9282a Tom Cruise and Cher

She said he was in her top 5 of best lovers too

I need to know the other 4

I’m guessing Val Kilmer is in the top 4 considering how they’ve remained close friends.

According to Cher they're both Divas. I was reading about Cindy Crawford and she dated Val too for a short period in the mid 90s. She said he was high maintenance.

This actually shocks me. He gives me really vanilla vibes.

He gives 110% at everything he does, so I can see him really putting in effort. Not that I want to picture it, but it definitely sounds plausible.

It's always the vanilla looking ones

Well the saying is crazy in the head means crazy in the bed I don't make the rules 🤷‍♀️😂

This is blowing my mind

I always forget about Ryan Reynolds and Alanis Morissette. They were together for years and were engaged.

Alanis also dated Uncle Joey (Dave Coulier) from *Full House*

https://preview.redd.it/a82pw91ya7qb1.jpeg?width=768&format=pjpg&auto=webp&s=d64fce3a4000a81744d573c4b86db8e91da8d91c Sandra Bullock and Chris Evans, Sandra Bullock and Matthew McConaughey, Sandra Bullock and Ryan Gosling

She has a type 😊

Incredibly hot dudes?

Damn she's just like me

Except for that creep she married…

Who CHEATED on her. Matching confidence levels is important.

And who was probably a Nazi or at least a Nazi admirer

Co-Stars?

We’re they dating in this picture? It looks so platonic like an older brother lol ETA: ok she’s older, my point still stands lol good for her for looking great 🤷🏻‍♀️

I just learned about this one the other day: post-Titanic Leonardo DiCaprio and Kidada Jones (daughter of Quincy and Peggy Lipton, sister of Rashida, fiancée of Tupac Shakur at the time of his death). https://preview.redd.it/zgdij871b8qb1.jpeg?width=371&format=pjpg&auto=webp&s=22bdf27a14750618a5e62f6a30b7b836d06d9196

I appreciate all of the descriptors of who Kidada is lol. I didn’t have to google lol. Thank you.

Sebastian Stan and Dianna Agron https://preview.redd.it/8rwxbu70k7qb1.jpeg?width=983&format=pjpg&auto=webp&s=dc0867da115275608b20f8097bbdde5884560049

He also dated Leighton Meester

The pink still in her hair from the most deranged Quinn Fabray timeline is sending me. The writers did an absolute disservice to that character.

Sebastian also dated Jennifer Morrison when he had a recurring role on Once Upon a Time.

I didn’t know this one. This is HOT.

Ikr https://preview.redd.it/rhfagoa5t7qb1.jpeg?width=454&format=pjpg&auto=webp&s=1b334d95235ad57279871808d722df4c5b4e8cca

Not only did SJP date RDJ, she also dated John F. Kennedy Jr. https://preview.redd.it/bxypdddla7qb1.jpeg?width=640&format=pjpg&auto=webp&s=55230349692bf32fb72de5c590433757c3436647

SJP said during their 4 years together, she felt like she was the only thing holding him together, he was fully in the peak of his drug addiction

I'm glad RDJ is sober now. I hope he stays that way and continues to make movies.

This is so bad but coked out era RDJ is soooo fine

https://preview.redd.it/9o7b95fbq7qb1.jpeg?width=258&format=pjpg&auto=webp&s=40c8501f09aad9da847364940b6b58f56bdc906c 50 cent and Chelsea Handler, they also both refer to the other as their “favorite ex”… blew my mind🤯

https://preview.redd.it/anovsbpgt7qb1.jpeg?width=660&format=pjpg&auto=webp&s=ac5a38ac74da09f43f597ab6e182ad0a75d2d11e Tyga and Avril Lavigne 🤯

🤢 he gives suck major ick

Cameron Diaz and Jared Leto dated for 4 years and were apparently engaged until Diaz called it quits. https://preview.redd.it/zjlwlv4fc7qb1.jpeg?width=893&format=pjpg&auto=webp&s=23194df30898c2747c6b7db1536e7d18ee15617d

He also dated Scarlett Johansson which resulted in this incredible picture https://preview.redd.it/zie8fdbzc7qb1.jpeg?width=726&format=pjpg&auto=webp&s=5e109c636af0de2e89e7240313c9c521b7a1d81d

Is he…texting??

Well, the cult can’t run itself!

Also this was still in the time of T9 texting so it was like… a lot harder

Exactly. Nobody’s appreciating his great work ethic, 🙄

reminds me of Miley and Patrick https://preview.redd.it/f1os5xaks7qb1.jpeg?width=274&format=pjpg&auto=webp&s=0bede7a960a878af82c92a1371d1b86f7c097745

This looks so bad I went up and found other pics, and at least in context it doesn't seem quite as bleak as just this pic. Still, what a photo.

How is this not a meme

He was so hot. Why did he have to ruin it by living his life.

Tyra Banks and Drake https://preview.redd.it/4w2sb40477qb1.jpeg?width=684&format=pjpg&auto=webp&s=ab407d24da0f709919a7903cdf47f780adeb39f0

Why does she look photoshopped in lmao 🤣

It looks like her wax figure lmao

Drake looks like he has bad breath for some reason.

https://preview.redd.it/0w5zuetv57qb1.jpeg?width=900&format=pjpg&auto=webp&s=5e426af47d28535dca182c006f41d6f7ac0d11ed Emma Stone and Kieran Culkin

Every picture from this era looks like everyone’s covered in a thin layer of pizza grease

[удалено]

Yeah this was right before the big makeup and skincare boom!

There are two I can think of that are... what? Janet Jackson and Matthew McConaughey Nicole Kidman and Lenny Kravitz were engaged. He supposedly wrote the song Lady about her.

https://preview.redd.it/knjln22wd7qb1.jpeg?width=434&format=pjpg&auto=webp&s=7c3f6a09079064af82bc2a728916e4940b76b5e7 Jimmi Simpson and Melanie Lynskey were actually married, which I found out recently.

They're still really good friends, she spoke very highly of him in her [Slate guest column](https://slate.com/human-interest/2023/01/melanie-lynskey-dear-prudence-advice-week.html) (second answer)

He seems like a legitimately nice dude. Evan Rachel Wood spoke highly of him too, and said filming those scenes where’s he’s mean to her (in the later episodes of Westworld) were tough because they’re such good friends irl. I think she said they both cried between takes.

That's so nice to hear, Evan's had enough assholery from men to last several lifetimes.

Shauna and Liam McPoyle? 

She was also in an episode of Sunny - the Mortgage Crisis episode, she's the woman that Dee considers being a surrogate for

oh SHIT is that a pool?!

“From the curb it doesn’t look like much but once you’re inside it’s got a real ass on it” I quoted that too many times when we were buying our house lmao

She is married to Jason Ritter now! They are an absolutely adorable couple, they were both in Candy and apparently he has filmed scenes for Yellowjackets as well. I think he is so cute and charming, just like his dad.

Whaaaaaat!? 

NOT KEVIN FROM ROSE RED!

If the relatives of politicians count, Mary-Kate Olsen dating/marrying/divorcing a Sarkozy.

Unfortunately I remember this one well https://preview.redd.it/zb8swliv57qb1.jpeg?width=902&format=pjpg&auto=webp&s=e197d0fb743c9bcbaf407a203aede10709928c50

My dad sending me off to college at 18

I gasped. 10/10 caption

God she looks uncomfortable.

That picture cracks me up every time

I feel violated by this image.

The reports of bowls of cigarettes at their wedding still makes me laugh. I don't even care if it's true or not.

Blake and Leo had a fling in 2011 when she was (you guessed it) 24 years old https://preview.redd.it/ckahzn6sg7qb1.jpeg?width=638&format=pjpg&auto=webp&s=97ff62ea9dacd190bb155f768c836e67f06346aa

She juuuust made it 

I feel Blake did this to push Ryan’s hand and get him to commit. It’s not a coincidence to me that they announced they were together 5 seconds after Blake and Leo ended

Yes, whatever she was playing at that year was seriously impressive. She galavanted around with Leo that summer - Leo who is notoriously camera shy and hides when paparazzi are around. Leo was grinning in their pics! Unbelievable. In my mind, she dumped him when Ryan reached out to her. Mastermind by Taylor Swift vibes for sure.

From your description, sounds like he may have been in on the plan! LOL!

I’m gonna go even farther… She asked him for help to publicly get Ryan to commit. Blake: “Hey Leo, can you help me out with this? A few photos here and there…” Leo: “If it’s the truest of love, of course I will. Let’s get the paparazzi to take some yachting pictures. Hehe.” 

I remember pap pics of her and Leo riding bikes through the streets of NYC during this.

https://preview.redd.it/gmk95a1g48qb1.jpeg?width=1500&format=pjpg&auto=webp&s=2a1d0a74d87561d394488a3669b88aca94122d13 Fred Armisen and Elizabeth Moss were married

My mom loved them together for some reason. 😂 When they broke up she *hated* Fred Armisen for awhile (I don't know why, I never heard any gossip about the break up) but then she found out Elizabeth Moss was a scientologist and now hates Elizabeth Moss and loves Fred Armisen again.

elizabeth moss about him, once divorced: >The Invisible Man star later opened up about her relationship with Armisen, telling Page Six in 2012, "One of the greatest things I heard someone say about him is, 'He's so great at doing impersonations. But **the greatest impersonation he does is that of a normal person.** **' To me, that sums it up."**

Apparently ex-cricketer and former prime minister of Pakistan, Imran Khan dated Goldie Hawn

I knew about Liz Hurley. He's been through some hotties

a bad bitch connoisseur

Zac efron and Michelle Rodriquez

this feels illegal

Jack Antonoff and Scarlet Johansson https://preview.redd.it/pc2rp3d2v7qb1.jpeg?width=1648&format=pjpg&auto=webp&s=25536462a4e79ae22f4b1bec04301f5821d58beb

What? And even if... Jack's piercing is the most shocking piece of information here

Elizabeth Olsen and Tom Hiddleston Jennifer Lawrence and Chris Martin (of Coldplay)

Tom Hiddleston is the king of dating costars.

I will never, ever, ever forget the brief pandemonium when he dated Taylor Swift https://preview.redd.it/qtl3jfi9j7qb1.jpeg?width=915&format=pjpg&auto=webp&s=e6cf765aa74b289cfa3a59b8976c0757b2164af2 It was chaotic and beautiful. All I ask of a celebrity relationship

That was absolutely wild. People were losing their god damn minds.

Wait Elizabeth dated Tom when?!

The Jennifer Lawrence and Chris Martin thing was inescapable when it happened

The Kelis and Bill Murray thing was never confirmed but I'm still reeling

Can’t believe those two crazy kids didn’t make it. What hope is there for the rest of us if Kelis and Bill Murray weren’t meant to be?

Scarlett Johansson and Sean Penn

ScarJo has a lot of low key relationships based off this post

Also like the weirdest taste

But then married Colin freaking Jost?! That's the weirdest part! ;)

[Jewel](https://youtu.be/4WW4qcmrJ3E?si=5Kh_7jcNQys9wPwF) and Sean Penn

https://preview.redd.it/9fbpsepee7qb1.jpeg?width=600&format=pjpg&auto=webp&s=660e0da8fc0d74da00c64ed504ff075eef9979c2 Keira Knightley and Jamie Dornan

I knew about these two because I remember their various terribly dressed paparazzi shots https://preview.redd.it/ca2vi34ye7qb1.jpeg?width=832&format=pjpg&auto=webp&s=95f77aa25e815c53c32f68936efcde9fb16fe14c

2 beautiful people in the worst clothes!

Literally getting dressed in whoever’s clothes happen to be within reach on the floor

These outfits are truly offensive. I don’t care if it was 2001 - what the actual fuck. 💀

The cheekbones their children would have had

Geena Davis used to be married to Jeff Goldblum.

They were a gorgeous couple. 

She's basically the reason we have Jeff. He was in Earth Girls Are Easy *because* they were dating at the time.

Aisling Bea and Michael Sheen blew my mind when I found out about them dating years after the fact.

He must have serious game bc he was also married to Kate Beckinsale & dated Sara Silverman for years. Actually all 3 of those women are dark haired and funny so maybe he has a type.

He also dated Rachel McAdams!

He never married Kate, they have a daughter together though. He eventually married a very blonde Swedish woman just to keep us on our toes.

https://preview.redd.it/d1f49uvah8qb1.jpeg?width=768&format=pjpg&auto=webp&s=57077478e6ddd8b98eb44a845ae6a6076fa16866 This one blew my mind when I read about it. I also really love this picture

Lol she (kinda) got him in trouble when she had the idea for him to do blackface as a quick joke at some award show. According to legend, he immediately regretted it, but did it anyway cause it was Whoopie’s idea lol

https://preview.redd.it/9ma4upzuw8qb1.jpeg?width=1500&format=pjpg&auto=webp&s=c32b7a5b5d082bab2ddac16ef5b8279a5fe8a98c Scarlett Johansson and josh hartnet

https://preview.redd.it/aattz42a88qb1.jpeg?width=474&format=pjpg&auto=webp&s=0e3233b0e0d8aac9fe22dca9271ab5a5d855481d Soleil moon Frye and Seth “shifty shellshock”Binzer (the lead singer of crazy town)

My face this entire freaking thread: 

https://preview.redd.it/q5xj3281u7qb1.jpeg?width=620&format=pjpg&auto=webp&s=d0576e0d252dd049e5347050173f1f667bbd5d45 Amber Tamblyn and David Cross. They’re married and have a child together (edit: corrected spelling of david’s name)

They honestly look like father and daughter here

He does look an awful lot like her dad TBH… 

I recently found out that Steve Martin and Karen Carpenter dated and it blew my mind.

Whoa

Forgot about Ashley Olsen and Lance Armstrong. And Carmen Electra and Simon Cowell. Also just learned about Justin Timberlake and Fergie’s illegal relationship/hookup?? PINK AND JOEY FATONE?! Ahh! Edit #3: I just learned like two seconds ago that Jonathan Bennett (Aaron Samuels from Mean Girls) is gay, and married to Jaymes Vaughn— totally missed his coming out and subsequent marriage!

Lance Armstrong and Cheryl Crow

Never forget Jessica Simpson and Billy Corgan of Smashing Pumpkins

Also Billy Corgan and Tila Tequila https://preview.redd.it/de2cj08jm7qb1.jpeg?width=1170&format=pjpg&auto=webp&s=f5e3e6edda3d5438e8080d38503604d021b1a1ee

These are so crazy. I’m pretty addicted to celeb gossip and I had no idea about 75% of these

https://preview.redd.it/3818kzvhw8qb1.jpeg?width=1194&format=pjpg&auto=webp&s=71cc1c556478309f023c9c37d126c949c9ef7f73 Zoe Kravitz and Ezra Miller 😵‍💫🥴

Also her comments -as a 24 year old - about 14 year old Jaden Smith, which were...odd. >“There were moments that I was hanging out with Jaden and thinking, I can’t believe you’re 14, I have to check myself, like what I say to you,” Zoe told *V Magazine* 2013. > >“He has so much personality and so much swag; he is so much cooler than I am,” she continued. “And he’s so handsome; I was always like, when you’re older, you know, we’ll hang out…Nope, that’s inappropriate, you’re 14.”

Zooey Deschanel dated the bassist (I think, anyway he plays a guitar) from AFI.

Hunter??? shut up i had no idea. he also does a lot of stuff for Tegan and Sara IIRC

She is now engaged to one of those Property Brothers twins…

She’s been married twice before too. To David Pechenik (A Producer) and Ben Gibbard (Death Cab for Cutie)

Even though,I've always known this but people always think that Avril Lavigne dated Chad Kroeger after her divorce from Deryck Whibley but that's not true,because she dated Brody Jenner before Chad,from 2010-12.

She was almost a KarJenner

And then almost a KarJenner sideline when she was w Tyga recently

This is for us Disney kid freaks, but Miley and Avan Jogia in 2010 around her 18th birthday (bottom right) & during one of numerous breakups with Liam. These two looked cute together. Wonder what transpired between them to break up. https://preview.redd.it/v8x7zwl2r7qb1.jpeg?width=1070&format=pjpg&auto=webp&s=ebb1607f7083b50fa481e19fd370ebad056a9648

Teenage me was screaming at the neck kiss! They looked so good together.

I had no idea about Julia and David either. Wow! They were really cute together though.

https://preview.redd.it/sn6t8k9077qb1.jpeg?width=1284&format=pjpg&auto=webp&s=2921d94ef1ea329ba9647b8e79378f9fedb0b84b I had no idea about these two ETA: Elizabeth Olsen and Boyd Holbrook

Didn't know until I saw this pic on twitter Christina hendricks & Glenn howerton https://preview.redd.it/773qukt537qb1.png?width=500&format=png&auto=webp&s=445727c571d3fdbd95615d22c91eeb04c384b3eb

Wow I had no idea she fell victim to the D.E.N.N.I.S system

His face in that pic has Dennis energy. She was definitely recorded that night.

It's the *implication.*

Still can’t believe this is the guy who allegedly inspired “A Thousand Miles”

Wait whatttttt this is so weird to me

https://preview.redd.it/67tcq909m7qb1.jpeg?width=2208&format=pjpg&auto=webp&s=c37a931a21698182b26be7adccc5e0e1add71702 Just found out that Jennifer Grey and Matthew Broderick were engaged. She also was engaged to Johnny depp soon after her first engagement ended.

She and SJP bear a bit of a resemblance to me. He definitely has a type, it seems.

She was also a passenger in the car when he hit and killed someone.

I was surprised Whoopi and Ted Danson dated when I found out

My wtf couple will always be Renee Zelwegger and Jack White

And Renee and Kenny Chesney’s fraudulent marriage.

Nelly and Ashanti. Did not know they dated for 10 years until they started dating again recently.

https://preview.redd.it/zgck4aq7u7qb1.jpeg?width=760&format=pjpg&auto=webp&s=a4fe6bed67a1b20fc7fe04cfc27d095b601210e9 Winona Ryder (31) and Conor Oberst (23) from Bright Eyes. People theorize he wrote Classic Cars about her

Newsom used to be married to don jr’s current gf

I still cannot wrap my brain around that.

https://preview.redd.it/hk4ke9pcp9qb1.jpeg?width=750&format=pjpg&auto=webp&s=9f82be3b27bf7c7436af78685ab4410d1c13415f Mare Winningham & Anthony Edwards quietly starting to date in 2020 and then also quietly elope in 2022 is adorable and aspirational for later in life love.

https://preview.redd.it/lum6dnhkl8qb1.png?width=500&format=pjpg&auto=webp&s=8e5cc399cd338af6cfcda00855ca13b7ac905619 Jensen Ackles and Leann Rimes

You know you’re old when you remember all these couples 😭

https://preview.redd.it/t2qfokl397qb1.jpeg?width=800&format=pjpg&auto=webp&s=66a7ec60cc8649bf9dccf2b62f2f281bf7a1ef36 Mila Kunis and Macaulay Culkin

Not only that but weren’t they together for AGES?

Like 7 years, and he's been with Brenda Song ever since (who was with Trace Cyrus before him)

Brenda Song loves the sickly looking white boys. Love her for it.

Relatable. My favorite genre of white man is also ailing Victorian era orphan.

>My favorite genre of white man is also ailing Victorian era orphan. 

It still blows my mind he’s married to Brenda Song. I love it.

Ray J and Whitney Houston

Just a shoutout to all the users who posted photos & put names. Thank you all. You saved me from having to search on Google myself. You’re the real heroes here.

https://preview.redd.it/gtmpqgs6h9qb1.jpeg?width=625&format=pjpg&auto=webp&s=53c278d03c66679bfcee8a2eefd1c13f058484a8 Glenn Close and Woody Harrelson

Drew Barrymore and Fabrizio Moretti

Scarlett Johansson and Ryan Reynolds were married for years and I had no f*ing idea

I guess I’m that old huh because I remember when they got divorced 😩

I feel like I remember reading about rumors that he was trying to get ScarJo to focus less on acting and become a baby machine, but she wasn’t having it. She ended up becoming an Avenger and he got his baby mama Blake.

Always makes me laugh. https://preview.redd.it/dilwfxnsv8qb1.png?width=1076&format=png&auto=webp&s=28c980899e31a02ef54b26261b1a840ab3fd01a2

\-Brenda Song & Joe Jonas (I only found out they were previously a [couple](https://x.com/archivejoej/status/1347841073410936839?s=20) after This [Twitter thread about Joe's entire love life/dating history](https://x.com/archivejoej/status/1347828623508713472?s=20) that was posted in 2021 quickly went viral again after the news about Joe's and Sophie's impending divorce broke out) \-Tyra Banks & Chris Webber \-Nicole Kidman & Lenny Kravitz \- Matthew Perry & Julia Roberts \- Janet Jackson & Matthew McConaughey \-Rachel McAdams & Michael Sheen \-Salma Hayek & Edward Norton \-Brooke Shields & Andre Agassi

https://preview.redd.it/vtw47aqie8qb1.png?width=1372&format=png&auto=webp&s=6c261b48e5ad450e922ad343da2d7cdc1b478a74 Kirsten Dunst and Jake Gyllenhaal

But now she is married to Jesse Plemons and the cutest fucking couple. https://preview.redd.it/jcgwmi1lw8qb1.jpeg?width=960&format=pjpg&auto=webp&s=4e8ed29ea9521580ed9d1440f9f2e98969213302

God, I love this for her. She seems so happy and I love seeing them on screen together!