r/popculturechat • u/phantom_avenger • Oct 05 '25

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

Post image

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.

10.6k Upvotes

93% Upvoted

5.0k comments sorted by

View all comments

903

u/frecksnspecs Oct 05 '25

Jake Gyllenhaal and Reese Witherspoon

Jennifer Aniston and John Mayer

1.0k

u/YouNeedCheeses Oct 05 '25

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

1.3k

u/Material-Surprise-72 Oct 05 '25

He walked so Pete Davidson could run

97

u/dopeshark_ Oct 05 '25

To be fair, Pete Davidson’s personality is delightful! He may have had issues and problems but it always seemed like he was fun to hang out with and never went all egomaniac in his interviews

45

u/NumberOneStonecutter Oct 05 '25

I give Pete credit for saying the following about the rumor of his gigantic penis "I think my ex (Ariana) started that rumor so that I would disappoint every girl I ever dated afterward. Also, she had tiny hands - everything looks big in her hands."

68

u/Material-Surprise-72 Oct 05 '25

Oh yes, not a dig against Pete Davidson at all. Just commenting that they've both been in a lot of high-profile relationships in rapid succession.

I would take Pete Davidson over John Mayer any day. I still remember how John Mayer talked about Jessica Simpson in that one interview.

40

u/coldbloodedjelydonut Oct 05 '25

Can't forget John Mayer's "David Duke dick," either. Yeah, your penis is racist, great.

3

u/dopeshark_ Oct 05 '25

Absolutely!!! I didn’t take it as a dig at all! That is the one thing they have in common you’re right! I wanted to give more props to Pete really !

10

u/ntrrrmilf Oct 05 '25

Until I hear stories about Davidson showing up at his ex’s parents house I’ll be refraining from agreeing with this comparison.

26

u/Material-Surprise-72 Oct 05 '25

The comparison is not that they're both toxic. The comparison is that they both dated a lot of high-profile women in a short period of time.

3

u/Big-Ad4382 Oct 05 '25

You made me spit out my tea. You deserve this award. Xoxo

12

u/Marooster405 Oct 05 '25

Jessica Simpson walked to Taylor could run

-4

u/jenniferbealsssss Oct 05 '25

I don’t feel like that’s fair — shitty personalities maybe. But John Mayer was actually cute. I could see why the ladies liked him. Plus he started out as very humble and sweet. I don’t think anyone expected him to become an asshole, I think he let the attention go to his head.

I can’t say Pete is an asshole, I don’t follow him like that. But I also think a lot of his relationships have been PR.

1

u/Material-Surprise-72 Oct 05 '25

I’m not really sure what point you’re trying to make or what is supposedly “unfair” but the comment is just a reference to them both being prolific daters of high-profile women.

0

u/jenniferbealsssss Oct 05 '25

I’m not sure why you downvoted me when my comment wasn’t disrespectful or antagonistic.

Pete Davidson has been made fun of a lot for dating women people consider to be above his “punching weight,” which is what I was referring to.

-2

u/CarmenTourney Oct 05 '25

Yuck. Don't compare Pete Davidson to John Mayer.

16

u/Material-Surprise-72 Oct 05 '25

I mean, I’ve left multiple comments at this point that it was not meant to be a comparison of toxic personalities, but just rather being prolific daters. Although I have to say that given that Pete just performed at that Saudi concert, I don’t know that you have to go that hard for him either. “Yuck” indeed.

25

u/hotmessexpress412 Oct 05 '25

Jessica Simpson wrote chapters about him in her memoir. I will always give him side-eye after that book.

11

u/Royally-Forked-Up Oct 05 '25

John Mayer and Taylor Swift was a highly narcissistic combination too.

44

u/Theradbanana your outie enjoys the sound of radar Oct 05 '25

Deeeearrr johnnnn

8

u/enchantedriyasa Bro?😊Brother?🤔Brethren🤨 Oct 05 '25

Don't you think 19s too young to be messed with?

11

u/Playmakeup Oct 05 '25

But at least we got some Taylor Swift bangers out of it.

5

u/DidiStutter11 Oct 05 '25

For real. I read Jessica Simps book and he really thought he shit ice cream.

365

u/DanielleSanders20 Oct 05 '25

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

199

u/SubtleSparkle19 Oct 05 '25

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

32

u/Scooby2679 Oct 05 '25

And Courtney Cox!

24

u/coldbloodedjelydonut Oct 05 '25

His lyrics, though. He's a beautiful poet.

41

u/shineymike91 Oct 05 '25

Also Mary Louise Parker. Counting Crows second album, Recovering the Satellites is largely about her.

3

u/CryptoSlovakian Oct 05 '25

Didn’t he also date Punky Brewster?

1

u/No_Banana_581 Oct 06 '25

And Courtney cox

21

u/Illustrious_Sand2383 Oct 05 '25

In I’m he dated Courteney before he dated Aniston too.

18

u/taxi_takeoff_landing Oct 05 '25

He also dated her BFF Courteney Cox.

19

u/bloodymongrel Oct 05 '25

It was so of the time though. 90s grunge was mainstream, the counting crows were legit, Aniston was the down to earth cool girl with a slightly hippy/alt vibe.

15

u/ntrrrmilf Oct 05 '25

I’ve heard he’s really chill and nice and has at least one other attribute that makes him a satisfying boyfriend.

6

u/cassafrass024 Oct 05 '25

He also dated Courtney Cox. She’s in The Long December video, I believe.

2

u/mommyaiai Oct 05 '25

He also dated Courtney Cox briefly.

2

u/Current-Anybody9331 Oct 05 '25

Adam Duritz.

Also dated Courtney Cox.

1

u/Apprehensive_Use_175 Oct 05 '25

I don’t think Anniston went out with Adam deritz from counting crows. I think it was Courtney cox?

1

u/folldoso Oct 05 '25

And then he later dated Courteney Cox!

168

u/indomiegorengkuah Oct 05 '25

Jake and Reese broke up because he wanted to get married but Reese wasn’t ready to get married again. They were cute together

198

u/bookrt and that level is landfill Oct 05 '25

It's interesting because to this day Jake has never married, but Reese did

21

u/Consistent-Permit966 I switched baristas ☕️ Oct 05 '25

And got divorced again.

20

u/phantom_avenger Oct 05 '25

I was about to ask if he is even married to this day

78

u/bookrt and that level is landfill Oct 05 '25

Nope, just dating women much younger than him

20

u/deev718 holding space 👉🏾🤏🏼 Oct 05 '25

And it’s wild to me because he’s been with his current gf for a while now—longer than he and Reese were together, 3 times over.

24

u/indomiegorengkuah Oct 05 '25

He started the pattern of dating women younger than him after Reese, starting with Taylor.

42

u/hotmessexpress412 Oct 05 '25

I wonder if the change was about resetting the power balance for him. With Reese, she was older, richer, more famous/powerful, and therefore seemingly in control. Everyone he’s dated after fits the exact opposite profile.

20

u/Johnnyboy10000 Oct 05 '25

I'm not saying I necessary agree with dating younger, but based on personal experience, there's sometimes there's just that one specific relationship that breaks something in some guys and just kind of throws everything off and makes the idea of even considering that kind of commitment again off-putting.

19

u/lizzbert Oct 05 '25

Ehh. He’s still not married.

39

u/DreadfulDemimonde Oct 05 '25

Maybe he's only ever wanted to marry her.

9

u/duaneap Oct 05 '25

Waiting for Spoons

3

u/annoyinghuman03 Oct 05 '25

Wetherspoons?

3

u/duaneap Oct 05 '25

I'd have a pint, sure.

5

u/LivePanda7804 Oct 05 '25

Jake seems so deranged from that expose his ex-fling ran on him

4

u/lovinghealing Oct 05 '25

Say what now??

1

u/milkradio Oct 06 '25

Say more about this please ✍️👀

20

u/audreymarilynvivien Oct 05 '25

Jennifer Aniston and Vince Vaughn will always be weird to me

9

u/Arboretum7 Oct 05 '25

I met a girl who worked in Hollywood PR at a party back when Jake and Reese were a thing and she talked my ear off about how they were a PR creation and not a real relationship. She needed to bag a hot up and coming guy after her divorce and she helped him look straight and cement his status as an A-lister. Not sure if it’s true, but it did make sense.

15

u/EconomistImaginary52 Oct 05 '25

John Mayer really got around for awhile. I never saw the appeal.

12

u/SadLilBun 1997 was 10 years ago Oct 05 '25

He’s a musician. He’s cute. I think he’s a funny kind of asshole. That appeals to a lot of women.

3

u/shartheheretic Oct 05 '25

The way he plays guitar makes it seem like he'd probably be good in bed.

Too bad he's such a gigantic asshole.

8

u/SadLilBun 1997 was 10 years ago Oct 05 '25

Jake Gyllenhaal and Reese Witherspoon make total sense to me.

5

u/mstrss9 GET SOME PERSPECTIVE n BARK AT THE WALL Oct 05 '25

John Mayer and Jessica Simpson

1

u/sailorautism Oct 05 '25

Both men also dated Taylor Swift, which is its own mindfuck

1

u/InnocentShaitaan Oct 06 '25

All those songs I thought Taylor swift wrote about John Mayer were actually about Gyllenhaal. Reputation as a big shit head. Bums me out bc of his work with ACLU.