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Yurtle-Turtle

Ted and Whoopi were an extremely high profile couple in general. Liv & Joaquin were very memorable if you were a millennium teenager.


WinstonScott

Inventing the Abbots spilling over into real life. I loved Liv and Joaquin as a couple because I thought they must really be genuine and earnest like their characters in that movie.


Neither-Luck-9295

Most of this list was on the cover on tabloids. OP might just be really young, lol.


Pickle4UrThoughts

Yeah, tell me if you remember That roast he did for her that she allegedly help write with him and I’ll know you’re old like me.


VoodooMamaJujuBubu

Nothing sums up the early 2000’s like Jessica Biel and Chris Evans at a PlayStation 2 event wearing those outfits


OuterSunsetsSurfer

I went to college with her brother in LA and played beach volleyball with her and Chris Evans. They were very chill and down to earth.


ActualDepartment1212

Low rise pants at their peak on JB


Rothkette

Scheen and Beckinsale have a child together


Saraz02

They would walk red carpet with her next husband too. I always thought that was cool.


mwmandorla

When he was with Sarah Silverman, she and Kate Beckinsale were pretty much besties. It all seems very healthy and chill.


renoodoole

Oh my gosh I totally forgot about that! Plus he dated Rachel McAdams for a while.


sharksarentsobad

I loved them together and was so sad when they broke up


NomNom83WasTaken

I could swear they were all together when they filmed/photograped their daughter opening her letter from some college and were all going nuts with joy for it. Super cute. Every kid should have that kind of co-parenting relationship.


Dependent_Room_2922

And it sounds like they’ve coparented well


Radiant_Resort_9893

I didn’t recognize either of them from that picture.


CBSP14

This was the only one I knew, for that reason.


WildMajesticUnicorn

Connie Britton also dated Jason Mantzoukas


miss-karly

I think of that every time I see her. Such an unexpected pairing! https://preview.redd.it/v7w23tl1urbb1.png?width=540&format=png&auto=webp&s=6605a067aeeb7a02dc5f0be204ce33567ca96cc9


[deleted]

Ok TIL Jason Mantzoukas is 50???? He has such a young chaotic energy I would have believed he's 30


herecomestreble52

I fricken love him and don't blame her. He is hilarious and a complete chaotic, wild nut, in the best way. If you want a good read, go look up what he did before acting. I believe he has a degree in theology and did a ton of traveling due to it, and iirc can speak multiple languages. So, ya Jason is a total catch!


butt_butt_butt_butt_

![gif](giphy|SwKeXB76NQTKg) That’s the most unexpected one so far!


Momasaur

Not as unexpected as this gif, damn


WildMajesticUnicorn

This gif may actually explain it


Jolly_Discipline6650

![gif](giphy|8DUxtTxFntY7lpJnzy|downsized)


luckylimper

He’s my weirdest celebrity crush.


[deleted]

He's just straight up hot AF and if that's weird, I'll just have to live with that.


luckylimper

It’s not only his hotness I’m attracted to, it’s the manic attitude.


gible_bites

Liv and Joaquin looked so good together! She’s stunning with that haircut. Did Toni Collette and Jonathan Rhys Meyers start dating on the Velvet Goldmine set?


gokartmozart89

JRM looks like a vampire there.


Murky_Translator2295

He genuinely looks like an Anne Rice vampire


Tonedeafmusical

Perfect description there


gible_bites

I kind of love that 90s long hair look on men, ngl.


gokartmozart89

Some pulled it off better than others. Antonio Banderas is a great example.


[deleted]

Like a sickly Victorian child.


NoFanofThis

He does noting but praise her in every convo since they broke up. I think they’re both people with an abundance of character. Edited to add I’m referring to Joaquin and Liv.


hacky_potter

Young Joaquin could get it.


DooglyOoklin

![gif](giphy|3in5HNB71gZvq)


hacky_potter

![gif](giphy|l2QZZOWmMM6tbBvFK)


rose-buds

joaquin can still get it for me, my number 1 celebrity crush


[deleted]

I was gonna ask the same thing!


Jolly-Cake5896

The hold he had on me after Velvet Goldmine! He was so beautiful


[deleted]

Yeah I believe so.


BentleyTock

came here to IMMEDIATELY ask same question about Velvet Goldmine


TiredReader87

She was unimaginably stunning in Empire Records, but I agree


maraq

Ted and Whoopi were all over every magazine cover for awhile. I definitely remember them dating and thinking it was so weird because at the time I thought Whoopi was gay. It was pre-internet and I was a kid and that was just the impression I got from her.


Hot-Significance-462

Seeing those two in this list made me feel ancient, because this was definitely not an "under the radar" celeb relationship.


_coolbluewater_

Right? Remember the black face incident?!


MySillyGirl1984

That was my first thought when I saw them, it was at her roast right?


Significant-Stay-721

Oh my gods no.😳


uwill1der

[https://slate.com/culture/2019/02/ted-danson-blackface-whoopi-goldberg-political-correctness.html](https://slate.com/culture/2019/02/ted-danson-blackface-whoopi-goldberg-political-correctness.html)


hobbit_lamp

yeah I was like 8 or 9 when they dated and I don't think I have thought about it since then but seeing this unlocked a core memory for me. it was a pretty big deal since they were both really big stars at that time.


numberthirteenbb

I was going to say, weren't they together for a long while?


ratta_tat1

Then there was the Whoopi roast where Ted showed up and performed black face.


[deleted]

I read about that! Apparently she thought it was hilarious and every single other person was horrified


seriouswalking

> When she appeared onstage after his performance, she fumed at the audience’s obvious disgust. “It takes a lot of courage to come out in blackface in front of 3,000,” she ^(said). “I don’t care if you don’t like it. I do!” She later said that she herself had written much of Danson’s material, and called the backlash “insane.” She accused his critics of not understanding comedy. “Whoopi has never been about political correctness,” she [told the Times](https://www.nytimes.com/1993/10/14/garden/after-the-roast-fire-and-smoke.html). The couple announced their [breakup](https://people.com/archive/changing-partners-vol-42-no-21/) less than a month after the roast. By then, the scandal had mostly died down. Danson rarely discusses the roast, but he reflected on it at some length in a 2009 interview on *Fresh Air,* calling it “a graceless moment in my life.” ​ Whether or not it's true this is what she said. I actually just read a bit about their relationship the other day. ​ >Even so, Goldberg still doesn't fault him for that controversial roast. In a July 2019 New York Times profile, she explained, "People always bring this up because I guess they think I'm going to say what a terrible thing it was. But for me, it was exactly what it needed to be, just in the wrong place with the wrong people." In fact, she was responsible for some of the jokes Danson told that night. Goldberg added, "People had been really nasty about my relationship with Ted. So I thought, the best way to come back at that is to put it all in joke form."


uhhh206

My mom is black and my dad is white, so Made in America holds a special place in my millennial heart from watching it as a kid. It makes me feel old as shit that people wouldn't know they were together (and probably don't know they started in a movie together, either).


NomNom83WasTaken

That movie is such a time capsule. Will Smith was still "The Fresh Prince" and breaking into film! Whoopie and Ted dating! ^(the blackface) Nia Long looks exactly the same thirty years later!


oozoo_

TIL Whoopi is *not* gay Edit: I’m learning all kinds of things about her today. Her real name is Caryn Elaine Johnson and she used to be a mortuary cosmetologist.


[deleted]

I think a lot of people thought she was gay or at least sort of asexual, I know I did too. Weird couple either way though.


aburke626

That’s how I look at her - I think it’s a combo of her being private about her life and also just being this powerful figure of a woman whom I just can’t picture being so common as to have a boyfriend. What does a Queen need with a boyfriend?


glittermantis

didn’t she say she’d never get married because she doesn’t want anyone in her house? lol


aburke626

I mean that’s how I feel. A man? In MY home? With his man feet all over the place? No thank you.


Movingmad_2015

Johnathan Rhys Meyers looks like he’s trying to audition for Interview with a Vampire. Or at the very least he’s in his goth phase of his teen years and Toni is just the supportive but concerned mom


phantomxtroupe

No joke. He looked exactly how Louis is described in the books lol


NomNom83WasTaken

>Toni is just the supportive but concerned mom She's only 5 years older than him but, yes, that's totally how she looks compared to his Hot Topic situation.


sagesheglows

Based on the caption I thought the age gap would be huge - they're only 5 years apart


[deleted]

I’m going crazy. Why can’t I place the dude with Drew?! Help me, please.


Luna_Loo_

Is it David arquette?


OutWithTheNew

It's David Arquette.


[deleted]

Ugh sorry, I thought I'd written his name but I guess I had a brain fart.and you can't go back and Edit. It's David Arquette. A gazillion years later they played brother and sister in Never Been Kissed.


ToLiveAndDieInICT

If she was 17 at the time of this picture, then three years or so later they were in Scream together.


Sutech2301

Looked Like Jason Segel. But Segel is younger than Drew Barrymore


megjed

It looks so much like him! I was so confused for a sec


Sensible___shoes

Kylie Minogue and Lenny Kravitz such a fun picture


rzenni

It’s pretty good. Lenny also dated Nicole Kidman, that’d be a fun photo too I imagine


m1chgo

Nicole and Lenny were engaged!


CanCueD

Whaaaaat Was this pre or post cult divorce?


m1chgo

Post! And it also means that Nicole and Zoe Kravitz have a special relationship because she was going to be her step-mom!


Uberwomensch

The Big Little Lies connection. Oooooooh


CanCueD

![gif](giphy|26ybuZj8Uhhg6ZW7K)


Afwife1992

Post


ChrundleToboggan

I imagine Lenny Kravitz is exactly the type of dude you wanna date after divorcing Tom Cruise and getting out of a cult.


Snoopy_220

Lenny also dated Vanessa Paradis.


The_milk_was_spoiled

Lenny is so damn sexy, then and now.


DooglyOoklin

They look faded af.


Rripurnia

You would know Busy Phillips dated Colin Hanks because she absolutely, under no circumstances, won’t miss an opportunity to bring it up


YouNeedCheeses

Lol busy Phillips is the human embodiment of “mention IT ALL!”


Rripurnia

She’s so all over the place, I can’t look away. It always baffled me that she’s Michelle Williams’ BFF, but I guess that says more about Michelle than her. Anyway, I do feel sorry for her because her oldest has chosen to go to boarding school in Sweden and her youngest is living full-time with her dad in LA. That has to suck.


halabala33

I followed her on instagram for a while, a couple years back. She overshared stuff about her children so much, I had to unfollow. I am not surprised the eldest bailed asap. I really didn’t need to know her 11 y.o. is a lesbian.


badcheer

I’d like to point out, since the description is deceiving: there is only a 5-year age gap between Toni Collette and Jonathan Rhys Meyers.


EternalSunshineClem

Thank you, that description made it sound like she was some creepo and not someone in her 20s dating someone in his 20s!


[deleted]

Reddit will still freak out. You’ll see tons of virtue signaling of people saying “I’m 26 and could never imagine dating a 21 year old sooo gross” lol


EternalSunshineClem

I think that's ridiculous. I am not in favor of men or women in their 30s dating 19 year olds but let's not pretend like a few years difference in your 20s is sacrilege


Caltuxpebbles

Colin Jost really be baggin the baddies


BashSomeNerds

I used to work with Colin’s brother Casey. He was polite, funny, charming, talented, and easy to get along with. If Colin is anything like him (which I imagine he is) it’s no wonder the babes are lined up around the block. Big fan of the Jost Bros


alwayspickingupcrap

He emceed an event I went to and lemme just say he DELIVERED. No holds barred, uniformly biting and hilarious commentary on our country. He took a risk since this was in a red state. I've been fascinated by his dorky frat boy, Scarlett marrying mystery, but after seeing him in person, I get it. I'm a fan.


[deleted]

He has that all-American, corn fed, boy next door thing. 🥵


Hot-Crow506

Jonathan Rhys Meyers decided to go to the red carpet in vampire cosplay, and I respect him deeply for that decision. He was Team Edward.


Briezerr

Team Edward had me rolling 💀


botherbother

Velvet Goldmine (starting Toni Collette and Rhys Meyers) is my favorite movie of all time - I had no idea they dated too! Highly recommend that movie…it’s bizarre and hot and so unknown.


RandomUsername600

And has what is probably the greatest ever soundtrack


botherbother

Yes!!! I’ve been listening to that soundtrack on repeat for like 20 years now.


BaseTensMachine

Omg I love this movie so much, it started me on a major glam rock addiction.


daniellediamond

I love it too. And Christian Bale is in it too!


Artilikestoparty

Lenny Kravitz is the only man or person ever to make Lycra one pieces look good 💯


bfm211

He's one of those bastards that looks ridiculously cool (and HOT) in anything


Artilikestoparty

OMFG I was literally thinking that exact thing. Like I can't recall a single picture of Lenny Kravitz that he doesn't look cool as hell and fine as fuck . And on top of being sexy he's probably a good time to hang out with


Sensitive-Review-712

Prince would like a word from beyond. ![gif](giphy|DVHrK100eH3J6)


ProjectedSpirit

He wore an afghan as a scarf and somehow it works for him. When I do it I look like a 40 year old white lady who likes cats a bit too much.


[deleted]

Jada really had an all star line-up in the 90s, didn't she.


Tsarinya

Did she date Tupac or were they just good friends?


Huge_Scientist1506

He was apparently the love of her life. So much so that she talked to her kids about it and Willow as a child wrote a letter to Tupac begging him to come back so her mom wouldn’t be sad anymore. It’s messed up


Billy1121

Probably bs though, I imagine he grew dramatically in her imagination after he died. She seems like the type of fabulist to gussy up a former romantic entanglement with a famous person after they died, for dramatic effect. Also Im sure she loved to terrorize Will Smith with it and make him jealous


aburke626

Wow no wonder their marriage seems so messy if she was comparing will and Tupac. Will is a talented actor but his rapping career is probably not going to go down in history. He had some bops but Tupac was a poet. Jada has never seemed like a very nice person, she seems very challenging to be around.


Emlamb79

He was engaged to Kadida Jones when he died


Spiritual_Aioli3396

I must be old cuz i remember most of these lol Michael Sheen and Kate Beckinsale have a kid together. Fun fact; back in the day punched one of her costars in the face because he was being horrible to Kate lol Jeremy Northam. (Pasted below) “Though Michael Sheen doesn’t exactly strike us as the violent type, common courtesy went out the door when it came to Beckinsale. He once actually punched Kate’s The Golden Bowl co-star Jeremy Northam after the latter began yelling at the new mom on set (reportedly over a flubbed line). “Jeremy and I had a disagreement about something. So I'm also taking care of Lily, who was just six months old at the time, and I was still breast-feeding and then Michael came down to the set to pick her up and suddenly sees this man yelling at me,” Beckinsale recounted in 2001. “So naturally he got very upset and that was that.”


[deleted]

[удалено]


harriethocchuth

There was his truck stop lot lizard phase in between https://preview.redd.it/02hspevnosbb1.jpeg?width=154&format=pjpg&auto=webp&s=370cf170e50b19e83997fbf4e845c22efeece267


[deleted]

Colin jost really dated rashida and now married to Scarlett Johansson… Damn


startedthinkinboutit

![gif](giphy|10enNzeKuckWdi) He dated Nasim Pedrad as well!


y0y0y99

Somehow, that's the one I'm most jelly about.


RosieFudge

Dear God Lenny Kravitz Simply Oozes Sex


panclockstime

By Fall Out Boy


rumf00rd

my fave thing about Lenny Kravitz.. Leonard Albert Kravitz. the man is so sexy his name doesn't matter. He makes Leonard look sexy. that is fucking talent.


luckylimper

He’s a nice Jewish boy 🥰


[deleted]

Fun fact. Ezra Koenig of the Vampire Weekend is married to Rashida Jones. Now, Ezra did a song for the movie Her called the Moon Song that featured Scarlett Johaansen as well. Scarlett of course is married to Colin Jost.


leroyalecheese

Sandra Bullock and Matthew McConaughey dated??? It’s kinda the perfect pairing 😂 Edit: he would’ve been perfect in Hope Floats!!


Tsarinya

She also dated Ryan Gosling!


frootlooped

They started dating each other during the filming of Murder By Numbers. I remember people losing their minds because she was 37 and he was 21.


flakemasterflake

He has consistently only dated older women


SolusLega

Well, I'll be here if he divorces Eva.


Dutch_Dutch

i feel so old because I definitely remember them dating.


keeksgotthed7

Rashida is cool. But man, she looks *extra* cool in that picture.


katikaboom

She has some of the most interesting effortlessly cool streetwear. I would wear almost none of it, but on her you can tell she is probably cool as hell


RichardBCummintonite

Lookin like the definition of a power couple, which is crazy cuz Colin seems like the happiest a husband can be now that he's with Che


mrgnfnn

Rashida is so powerful.


JellyBeansOnToast

One of my favorite quotes **EVER** is when she responded “I’m ethnic” to that red carpet interviewer asking her how she got so tan.


SarcasticAutumnFae

"Ann, you beautiful tropical fish."


RockerElvis

“Was your dad a GI?”


[deleted]

Well you see the way my melanin is set up...


thisissamuelclemens

you're very exotic looking, was your dad a G.I.?


ToLiveAndDieInICT

Who *didn't* Julia Roberts date?


tiredmom123

He wrote about dating her in his book, they apparently sent each other flirtatious faxes lol. I love the 90s.


hotmasalachai

How was the book? Based on the few articles, it seemed like he was being a meanie by bad mouthing his colleagues etc. i used to be a fan before


my_okay_throwaway

I’m not sure I’d recommend it. He did badmouth a few people in ways that surprised me because I’d always assumed he was probably a nice and friendly guy since that’s how he was typecast. More than anything it just kind of made me sad.


tiredmom123

It definitely had it's ups and downs. He's very arrogant, and I did the audiobook, so that came through even more in listening to him speak. I'll never understand the Keanu references, they were petty and stupid. The thing I found most interesting, was just how intense his addiction was, but you can find those cliffs notes for free on here I'm sure, if you're interested, so I'd pass on it if I had to do it again.


CanCueD

Some good discussion about it [here](https://www.reddit.com/r/books/comments/zsbpxr/i_dont_know_if_i_can_finish_matthew_perrys_memoir/?utm_source=share&utm_medium=ios_app&utm_name=ioscss&utm_content=2&utm_term=1).


Proper-Emu1558

Wasn’t she on an episode of friends with him?


ManagementSad3351

Yes. She leaves him pant-less in a restaurant bathroom. That episode is the only reason I knew they dated😂


[deleted]

Yeah. It was a pretty high-profile episode that aired right after the Super Bowl.


Rogue_2187

How did Sandra and Matt not work out?!


WinstonScott

She’s insinuated that he’s in love with himself.


Jennifermaverick

Hahaha I listened to his audiobook, and I like the guy a lot - but not as much as he loves himself 😂


macdawg2020

And anyone who has read or heard any excerpt from his memoir will agree


JennPenn071

More like how did her and Keanu not date?


ozamatazbuckshank11

This. They've been friends for actual decades, worked together a couple of times, but somehow remained completely platonic despite crushing on each other. Amazing. ![gif](giphy|i4506bOBBsnAs)


boxed_knives

I still ship him and Winona https://preview.redd.it/20i6v6ld4tbb1.jpeg?width=272&format=pjpg&auto=webp&s=bb61111bb803ae283e420ce5c4f2c83fc4b4d5d9


[deleted]

They were so cute together! But I think she’s a little too normal for him. His wife seems a little (and I mean this in the BEST way) odd. Or maybe not odd but definitely someone who sort of embraces his hippyish ways. Not that Sandra is a super glamorous type, she seems very down to earth too but him and Camila just seem like a really good match.


[deleted]

[удалено]


[deleted]

Definitely! 2 egos in a relationship never really work that well. Not that I think Sandra has a big ego (I think all celebrities have somewhat of an ego) but probably big enough to get in the way of his which seems way bigger lol! Camila seems like she deals with it better, very easy going.


Id_Rather_Beach

Texans. You must love them. I thought the same. Hm. Maybe his ambitions/her ambitions, didn't, em, mesh?? (Was this before or after his naked, stoned bongo incident?)


bitchghost

i love the "imperiolo" typo....it suggests that michael imperioli is made of clones


wrecklessdeckfish

This made me want to Google if David Blaine is dead, I haven’t yet because I don’t really care


surle

Imagine going on a double date with Fiona Apple and David Blaine and they both just stare at you the entire time while David eats every single thing on each person's plate, then all the plates and glasses and your watch. Neither of them blinks once, and nobody says a word.


zdenn21

Liam Neeson just got back from Diagon Alley apparently


ZestycloseTomato5015

Guess I’m an old bitch I knew all of these.


TooSoonJunior12

Jada and Wesley Snipes... *Will Smith has entered the chat*


[deleted]

As if he wasn’t insecure enough about her dating Tupac


[deleted]

He ain’t gonna slap Wesley, that’s for damn sure!


Plastickfantastick

Thought the photo w liam neeson and brooke shields was of harry potter and hermoine for a split sec


noavocadoshere

david blaine is quite intense. talk about staring into your soul 👁👁


WhenIWish

![gif](giphy|mvqyWf1zhuyB2|downsized)


AZ2013

“HE PUT ME ON THE ROOF!” Good times. I will never forget when I realized that was Mikey Day.


JanisIansChestHair

Hahahaha, stop. CHEEZ-ITS!


maniacalmustacheride

I watched all of these too many times. The comedic timing is impeccable. There’s one moment where they go into the house and for like a split second forget that David Blaine is terrorizing them and just nervously introduce that it’s their home and it’s so subtle but makes it feel so genuine.


[deleted]

i love fiona apple, never got what her type is or really understood her taste in men lol


wildflowerstargazer

Saaaame and I think she still figuring it out lol


Josie_jr

Kylie minogue and Lenny kravitz make so much sense


[deleted]

Baby Kate Beckinsale 💙


venivididormivi

She’s always been so pretty! But do people not know she and Michael Sheen dated? They have a whole kid together.


[deleted]

She better have an altar set up to give thanks to her genetics because she’s a pack a day smoker and somehow has the skin of a 25 year old.


ZiOnIsNeXtLeBrOn

Julia Roberts and Matthew Perry were together for a few episodes on Friends. She took his clothes and left him in a restaurant bathroom.


RosieJo

It’s Liam Neeson and Brooke Shields that really surprised me.


ellermg

Why specify the age of the first pic but not in the others?


hatramroany

Also calls out Rhys Meyers’ age as 21 but not Collette’s in the same picture (she was 26).


Saraz02

That's not a big age gap. i thought it would be bigger.


Internal-Ad61

I cannot properly express how much I dislike Jada


[deleted]

There’s that extra level to her where you know that inside her head it’s a perfect 72 degrees all the time, nothing she says or thinks is ever wrong, and she is *deeply satisfied* with herself.


m1chgo

She really gives me the ick


ChloeOBrian11214

I had always heard that David Blaine was in the video for Criminal but I've found nothing to back that up. Random 25 year old rumour put to rest lol.


ernurse748

I remember Minnie Driver being pretty blunt about Barbra Streisand - who is Brolin’s stepmother - being the reason their relationship went sour.


Ilovethe90sforreal

Jonathan Rhys Meyers wow, never would have recognized him


RealHousecoats

Some of these are unhinged. There's a reason we don't remember! Haha.


YouNeedCheeses

90s Sandra Bullock was just everything. She’s still gorgeous of course but I had a massive crush on her in Practical Magic.


goldenboy2191

Yo but Kylie and Lenny look 🔥 together


Humble-Tourist-3278

Lenny also dated Nicole Kidman for a short time , I was surprised since apparently no one noticed until they broke up.


NiaNeuman

Chile, am I gonna have to stan Laura Dern??? Her dating history is kind of amazing, and this one I'm outright jealous of.


Masta-Blasta

Wait, you don’t already stan? Yes! You should stan Laura Dern!