Celebrity Relationships That Will Make You Feel Uncomfortable

By molly atherton 1 year ago

1. Harry Styles and....

Image Source: StyleCaster
Olivia Wilde. Wait, no, Em Rata. Wait... Okay, we should start by saying that this uncomfy list of couples may not CURRENTLY still be together, but they've definitely made us feel some type of way. Many speculated about Harry and Olivia's relationship, because it was so soon after her split from Jason. And then, after they broke up and Harry was publicly making out with Em Rata (who's supposedly Olivia's friend), everyone was SO confused!

2. Ashley Olsen and Lance Armstrong

Image Source: RadarOnline
People were pretty surprised when these two got together. Ashley and her sister, Mary-Kate, were known for their wholesome TV shows and films. After leaving acting, the pair became business moguls, especially in fashion. When Ashley started dating professional cyclist, Lance Armstrong, in 2007, no one saw it coming. In fact, Lance's friends told him that he should end things with Ashley because they had a 15 year age difference.

3. When Scott Disick dated Bella Thorne

Image Source: Glamour
So whenever you hear the name Scott Disick, you almost automatically think of Kourtney Kardashian and the rest of the clan. Scott's love life outside of Kourtney is interesting to say the least. But probably the most shocking and the one that made fans the most uncomfortable was his relationship with Bella Thorne in 2017. They were together for spring and summer of that year before they called it quits.

4. While we're circling the Kardashian crew...

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How are we still talking about these two? Granted, kids are involved, so that makes things more complicated, but Khloe Kardashian's relationship with Tristan Thompson makes people frustrated. They've broken up and gotten back together... Tristan has caused Khloe so much pain that most fans would rather she just stay far far away from him!

5. Did you know Tom Cruise dated Cher?

Image Source: BuzzFeed
Visually, this couple just seem mismatched to a lot of people. Tom was at the height of fame in the 80s with Top Gun, and Cher was a music icon. On paper, it made sense, but seeing them together left a lot of people scratching their heads. Cher said in an interview once that Tom was one of her Top 5 favorite lovers. That's high praise!

6. Lenny Kravitz and Nicole Kidman

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Nicole Kidman and Tom Cruise were married, and Nicole famously celebrated their divorce in 2001. Later in 2002, she was linked to Lenny Kravitz, who was initially her LANDLORD. The two eventually got engaged, but they never ended up walking down the aisle. Nicole said she wasn't ready, but that her thing is getting engaged and getting married. We love a self-aware queen!

7. Blac Chyna and Rob Kardashian

Image Source: E! Online
Even to this day, there seems to be a wake of DRAMA that follows Blac Chyna everywhere she goes. So it's fair to say that fans were not pumped when Rob Kardashian got into a relationship with her. The couple were fighting non-stop and so much drama came up between them. Not to mention the fact that Kyle started dating Tyga shortly after he and Blac Chyna broke up.... MESSY!

8. Angelina Jolie and Billy Bob Thornton

Image Source: Reddit
Before Brad Pitt entered the scene, Angelina Jolie had a relationship with Billy Bob Thornton. Their relationship began when Billy cheated on his girlfriend, Laura Dean. Not off to a good start, and also sounds vaguely familiar? After that... they did weird things that made people uncomfortable, like wearing vials of each other's blood. So, yeah.

9. Jessica Simpson and John Mayer

Image Source: Reddit
People literally watched Jessica Simpson's relationship with Nick Lachey unfold on national television. So when the two split and she moved on with John Mayer, people had a LOT of opinions. The couple broke up and got back together various times, and Jessica's fans never really supported the idea. John made some explicit comments about Jessica in an interview, which just added fuel to the fire.

10. Pink and Joey Fatone

Image Source: Perez Hilton
So, according to Joey, he actually asked her out a few times. And he was friend-zoned. We know how that goes, bud! They went out, finally, but he said he thinks that he wasn't her type. So, guess it just didn't click for these two. Love them both, but we can kinda see why?

11. Is this what broke up The Beatles?

Image Source: Wikipedia
While Yoko Ono and John Lennon didn't make anyone uncomfortable because of massive PDA or weird vials of blood, people often accuse Yoko of being the reason The Beatles broke up. It's hard to say whether or not that is true, but it did cause many people to never like Yoko Ono.

12. Cara Delevingne and Ashley Benson... no, wait

Image Source: Page Six
People were pretty obsessed with Ashley Benson and Cara Delevingne relationship. So fans were not happy when Ashley was seen out with G-Eazy before the breakup was even officially confirmed. Fans were calling Ashley out, so much so that Cara had to step in and ask fans to leave her alone.

13. Madonna and WHO?

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Lol. Remember when Madonna and Dennis Rodman dated. Ah, the 90s, where anything was possible. Sure, these two only made it two months (no surprise there), but they took us on a ROLLER COASTER of emotions during those two months. My only question is.... Why? No, seriously. Why?

14. Don't shoot the messenger...

Image Source: Reddit
People feel uncomfy when it comes to Hailey Bieber and Justin Bieber's relationship. Now, I think a lot of people would agree that Justin's relationship with his famous ex was not particularly healthy for either of them. But for some reason, fans just can't accept that he's a married man, and he and Hailey seem genuinely happy!

15. Can't we just let these kids be happy?!

Image Source: Reddit
The other half of the Jelena equation hasn't had the best of times in new relationships either. When Selena Gomez started dating The Weeknd, fans were ~uncomfortable~. And it wasn't Sel's fans, it was HIS fans. The Weeknd famously dated Bella Hadid, and they wanted to see them back together, so they didn't like that he was moving on.

16. Lana Condor and NOT Noah Centineo

Image Source: Reddit
Fans have a way of wanting to see their favorite leading couples together off-screen and IRL. That was very true for Lana Condor and Noah Centineo after To All The Boys I've Loved Before came out. Fans were disappointed to know that the two were just friends and in fact, Lana was in a long-term relationship with Anthony De La Torre. Lana and Anthony have since gotten engaged!

17. Speaking of onscreen relationships IRL

Image Source: Us Weekly
Also within the Netflix universe, fans were over the moon when they learned that The Kissing Booth stars Jacob Elordi and Joey King were a real life item. The couple broke up amidst rumors that Jacob was dating his Euphoria co-star... Zendaya. Talk about tea! And then, post break-up, Joey and Jacob had to film TWO more movies together. Rough times!

18. Fans were NOT onboard with this couple

Image Source: The Mirror
Miley Cyrus and Cody Simpson were pretty public with their relationship. After Miley's divorce from Liam, the two posted PDA pictures all over instagram. Fans were not happy because they were hoping to see Miley and Liam reconcile. But at least the two of them were happy, I guess?

19. Harry Styles... again

Image Source: Quora
Harry Styles and Kendall Jenner dated on and off for YEARS. This left fans feeling annoyed by their relationship. Even now, fans are still commenting because a lot of people don't think that Kendall is a good person, based on various events, and so now they're annoyed that he's even friends with her! It's hard to keep up!

20. And then The Weeknd went and did this

Image Source: Reddit
As we already discussed, fans across the board were not happy about Selena Gomez and The Weeknd's relationship. They wanted to see him back with his old flame, Bella. THEN, he and Sel broke up... THEN, he and Bella got back together! Selena's fans were not happy (they rarely are). But Selena and Bella seem to be on good terms now!

21. Justin Timberlake and Fergie

Image Source: Us Weekly
It's hard to picture Justin Timberlake with anyone other than Jessica Biel at this point. Of course, he's had some famous exes like Britney Spears, but Justin and Jessica's admiration for each other has made them relationship goals. But back in the day, when Justin started dating Fergie, well... Justin was 16 and she was 23, so it was definitely ILLEGAL. Eep.

22. Tesla mogul with... Grimes?

Image Source: Us Weekly
This couple have since called it quits, but they definitely turned some heads when they took their relationship public. Tesla mogul, Elon Musk, and musician, Grimes, dated for a few weeks before attending the Met Gala together. They stayed together for a while and even had a baby boy together. Fans did not love it.

23. Madonna and Tupac

Image Source: BuzzFeed
Way back in the 1990s, everyone was speculating about a passionate relationship between Tupac and Madonna. Madonna later confirmed the rumors saying he got her riled up on life. She also said that she was really feeling herself when she was with him. At the time, people found it uncomfortable, but a letter later released from Tupac to Madonna gave more insight into their relationship.

24. Chelsea Handler's favorite ex

Image Source: Twitter
Did you know that Chelsea Handler dated 50 Cent?! Yes, you read that right. This couple definitely raised some question marks when they started dating. They were only together for a few months, but Chelsea says that he's still the ex she's asked the most about, and she said he's her favorite ex. She even calls him her big fat teddy bear.

25. You either love them or hate them

Image Source: Reddit
Megan Fox was married to Brian Austin Green, and when they announced they were separating rumors started swirling around her relationship with Machine Gun Kelly. The two have been in a relationship for a while now and love to show PDA any chance they can. However, this couple leaves a lot of people with the ick. What about you?

26. It's gonna be a no from Simon Cowell

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Fans were shocked when Carmen Electra and Simon Cowell took their relationship public. The two met on Britain's Got Talent and were together for half a year. It didn't end well for these two when Carmen caught Simon in bed with another woman, Lauren Silverman. Simon and Lauren are actually still together and have a couple of kids.

27. Zac Efron making out with Michelle Rodriguez

Image Source: Reddit
People thought that Zac Efron and Vanessa Hudgens were endgame. A Disney couple that everyone loved, but sadly they broke up in 2010. So people were not loving it when a few years later, Zac was caught in some serious PDA with Michelle Rodriguez on a trip to Ibiza. The couple have an almost 10 year age difference and only dated for a couple months.

28. Another Scott Disick WTF moment

Image Source: Hollywood Life
We already talked about Scott's relationship with Bella Thorne that left a lot of people feeling awkward. But, beyond that... two years after Kourt and Scott broke up, Scott began dating Sofia Richie. She was only 19 at the time, and he was 34. No one was comfortable with this relationship!

29. Naya Rivera in Hawaii with who?!

Image Source: Us Weekly
This news had people up in arms when it first hit the internet. The late Naya Rivera was spotted with none other than David Spade back in 2017. The two were seen at a resort in Hawaii, and many fans spotted the two making out pretty publicly in the pool at Halekulani Hotel. And that's what you missed on Glee.

30. Brad Pitt and Angelina Jolie

Image Source: Reddit
When we say that people were OBSESSED with Brad and Jennifer Aniston together, we mean it. Jen was the absolutely stunning and perfect girl next door and Brad was the Hollywood hunk. People were devastated when the couple announced they were divorcing. So when Brad quickly moved on with his then co-star, Angelina, people felt uncomfortable. Now that Brad and Angelina have split, do you want to see a Brad and Jen reunion?

31. Kylie Jenner and Timothee Chalamet

image source: glamour.com
The Jenner clan gets around, doesn't it? It started out as mere rumors that Kylie Jenner and actor Timothee Chalamet could be dating - but then it turned out there could actually be some truth to the rumors when they'd been spotted and apparently getting to know each other... it's just the most random match in the world, isn't it?

32. Matthew Morrison and Kristen Bell

image source: buzzfeed.com
You might never have really known actress Kristen Bell without Dax Shepherd, because it feels like the pair have been together forever. But a long time ago, Kristen Bell was dating Glee actor Matthew Morrison - and apparently it's the reason she likes Glee so much...

33. Kat Dennings and Josh Groban

image source: buzzfeed.com
Even this picture looks weird! Such a random couple we never knew happened - and never wanted. Apparently it was their 'humor' that made them think they were a match made in heaven, because Groban was impressed by the actress's taste in comedy. Their relationship lasted for 2 years.

34. Jennifer Lawrence and Chris Martin

image source: ndtv.com
Chris Martin was best known relationship wise for being with Gwyneth Paltrow, but it seemed he moved on pretty quick to the next pretty blonde: actress Jennifer Lawrence. The pair were spotted out and about while they dated, but they ultimately split because of 'schedule conflicts'.

35. Jared Leto and Cameron Diaz

image source: buzzfeed.com
Did you even know this happened? This is so random! It looks like Jared even dyed his hair to match his bae. They actually dated for four years, which is even more shocking because by Hollywood standards that's a lifetime. They somehow managed to keep it on the low-key, too!

36. Seth MacFarlane and Emilia Clarke

image source: buzzfeed.com
Mother of Dragons and Mother of Surprising Relationship Twists, because we never saw this coming - or even knew it happened. This pair apparently dated for around six months before the actress and Family Guy creator called it quits, apparently because of how much she was moving around filming for Game of Thrones!

37. Taiki Waititi and Rita Ora

image source: buzzfeed.com
Even though this pair are still married, and look happy at that, there's no denying we all felt a little weird when we heard they were officially a couple. It's just the last pairing you'd expect out of nowhere, really. They first met in 2018 and seemed to have happily been moving forward since.

38. Jennifer Lopez and Ben Affleck

image source: buzzfeed.com
Look, we know these two were together, split up, then got back together and seem loved up but there's just something... off about it. Maybe it's because Ben just looks fed up in every single photo he has taken of him and J-Lo. It was all just a whirlwind of her going back to Ben and then marrying him!

39. Mark Ronson and Rashida Jones

image source: buzzfeed.com
Pictured here looking very young, the DJ and actress actually dated - and they not only dated for many years, but they were even engaged! Such a random celebrity pairing. Mark proposed to Rashida in 2013 and she said yes, but then the pair split a year later - amicably, though.

40. Taylor Swift and Tom Hiddleston

image source: buzzfeed.com
We all remember the 'I heart Taylor Swift' tank top drama, don't we? It was weird then, and it's still weird now. We know now that this was likely a rebound situation after Taylor splitting up with Calvin Harris, but it was a fleeting romance that made enough weird headlines when it happened!

41. Zach Braff and Florence Pugh

image source: buzzfeed.com
Even though the relationship was obviously serious and Florence continually spoke out in Zach's defence, their fandom made their thoughts known about the huge 20 year age gap between this pairing. They lasted a few years and it seemed as though they were going to beat the haters, but they ultimately split.

42. Meghan Markle and Prince Harry

image source: buzzfeed.com
This is one we definitely didn't see coming, and we haven't heard the last of it since. It's gone from drama to drama since royal Prince Harry started dating American actress and Suits star Meghan Markle, of all people. At first it seemed like they were going to work well in the royal family... until they didn't.

43. Kanye West and Julia Fox

image source: buzzfeed.com
This one was a whole month of weird and even weirder denim, when it turned out that Kanye West and Julia Fox were dating when they were spotted around Manhattan together. The weirdest thing about it was that it kind of made sense... in a weird way.

44. Pete Davidson and Kim Kardashian

image source: people.com
This one was completely unexpected, but it was so weird that we actually sort of wanted it to work just to see how they'd get on. Well, it didn't last very long, and it turned out that ex Kanye West wasn't too happy about it, either... so it didn't really set a strong foundation.

45. Katie Holmes and Jamie Foxx

image source: harpersbazaar.com
This couple was made all the more weird because not a lot of people knew they were together - maybe this is news to you even now. They managed to keep it very quiet, and it's just an odd, unexpected pairing that nevertheless lasted for six years before they called it quits!

46. Lizzy Caplin and Matthew Perry

image source: dailymail.co.uk
You might not have pictured Matthew Perry with anyone other than Courtney Cox (they were never together, of course, but their Friends chemistry was just too darn strong). But Matthew was actually dating actress Lizzy Caplin, and they called it quits after he apparently didn't want to get married!

47. Kristen Stewart and Rupert Sanders

image source: hollywoodlife.com
This relationship - or, rather, affair - hit the headlines after Kristen Stewart was photographed getting cozy with director Rupert Sanders, while she was dating everyone's favorite vampire, Robert Pattinson. At the time, Kristen was 22 and Rupert was 41 years old - and also married with kids.

48. Katie Holmes and Tom Cruise

image source: usweekly.com
Another cringe from Katie Holmes and Tom Cruise separately - and here together - we all remember that very strange Oprah interview and how her couch got a beating after Tom decided to jump up and down on it. All in the name of love, right? Until they split, of course.

49. Whitney Houston and Bobby Brown

image source: themirror.co.uk
This relationship makes everyone feel uncomfortable in hindsight when the truth was unravelled after Whitney's death about her turbulent marriage to Bobby Brown. Bobby apparently enabled her drug problems, amongst other things, and it was all extremely tragic.

50. Miley Cyrus and Liam Hemsworth

image source: elle.com
This shouldn't have been weird, and it wasn't at first, but now it's just got weirder and weirder since the divorce. The couple were very much on again/off again, expecting us lot to keep up with it all, until they officially called it quits, and now turns out they weren't too happy to begin with...