The Weirdest Celebrity Couples You Never Knew Dated

Celebrities, they’re just like us. They eat, sleep, and have questionable dating pasts. Celebrities constantly break up and get back together, making it hard to keep track of who dated whom. Just like your friends who never fail to bring up your relationship mistakes, I am here to remind you of the weirdest celebrity couples you never knew dated (or you completely forgot).

1. Mila Kunis and Macaulay Culkin 

I think this is probably one of the weirdest celebrity couples on our list, if not the weirdest. Not only did Mila Kunis and Macaulay Culkin date, but they were together for eight years! I know, right! Their relationship ran from 2002 to 2011, starting when she was just 19 and he was 22 years old, taking up a major chunk of their adolescent lives. Although their relationship may seem random af now, it wasn’t so strange when it began. Culkin was still ridiculously famous from his Home Alone days, while Kunis was staring in That’s 70s Show. They were basically teenage royalty, a celebrity power couple if you will. But tbh, it’s hard to imagine a time when The KuKus weren’t a thing.

2. Tom Cruise and Cher

Oh baby, this couple was a strange one. Back in the 80s, these two (with a 16 year age difference, might I add) had a fling. Cher has said that Cruise is “one of top five former lovers,” so good for you, buddy. But I can’t help but wonder if that got his ego going, resulting in his downward Ross Geller-inspired spiral of marrying, divorcing, repeating? But hey, who am I to judge? At least Cher got Tom pre-Scientology.

Tom Cruise

3. Ryan Gosling and Sandra Bullock

Another odd that made it onto our list of weirdest celebrity couples is Ryan Gosling and Sandra Bullock, with another 16 year age difference. Why is 16 the magic number?? Anyway, back in 2002 these two had a year-long relationship before Gosling married Eva Mendes in 2011 and Bullock married Bryan Randall in 2015. Though their fling was short-lived, Gosling did say that Bullock was one of the best girlfriends he ever had. Aw.

4. Jennifer Aniston and Paul Rudd

Rachel and Mike? WTF. Girl code specifically states that “one should not date their best friend’s past or current boyfriend or husband” (or something like that). The fact that Jennifer Aniston dated Phoebe Buffay’s husband is soooo not okay. The two dated while filming The Object of my Affection in 1998. Although Phoebe and Mike didn’t start dating until 2002 (Season 9, episode 3), it just seems wrong for all us Friends fans out there.

Jennifer Aniston Paul Rudd

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6 Strange Celebrity Couples That Somehow Work

Love in La La Land never seems to last, but you would think couples like Brad and Angelina and Channing and Jenna would’ve been together forever since these Hollywood romances were legit #couplegoals. So maybe dating the person who seems absolutely perfect for you isn’t a recipe for long-lasting romance? Odd couples seem to be where it’s at these days, and honestly, we’re kind of into it. Not just because we’re happy for them, but because we live for celebrity gossip we do not see coming. Check out some of these weird celebrity couples and why they actually work. Maybe there is hope for you and Zac Efron after all.

1. Ariana Grande and Pete Davidson

Ariana Grande and Pete Davidson are without a doubt the weirdest couple to break headlines this year. The SNL star and his ex-girlfriend Cazzie David seemed like a match made in comedy heaven since her dad, Larry David, created and wrote Seinfeld and Curb Your Enthusiasm, which are the funniest shows of all time (according to your dad). However, Pete confirmed their recent split. At the same time, Ariana Grande and her rapper beau Mac Miller broke up as well, citing that they’re “better off as friends.” In other words, some shit went down and they definitely do not want to see or speak ever again because “better off as friends” is the most bullshit excuse of all time for a breakup. So it only took a hot minute for Ariana and Pete to rebound with each other, and the internet was collectively all, “What the actual fuck?” Ariana Grande seems to take herself super seriously, so it would be surprising if she was chill with Pete using her antics as material for his stand-up routine. She’s used to guys bowing at her feet. I mean, how can you forget that time Big Sean rapped that Ariana was “a million dollar chick with a billion dollar pussy?” And it’s equally as surprising to think that Ariana could write “Side to Side: Part 2” about someone like…Pete Davidson. But you know what? They may be different, but they’re complementary. Ariana Grande is so self-involved that her entire Instagram is pictures of her Blue Steeling for the camera on her own, and Pete could probably teach her to lighten up and stop being so narcissistic. He already had her shake things up with their oh-so-adorable Harry Potter couple pic. Also, Ariana’s impressions put every SNL cast member to shame, so she could definitely give Pete some tips on how to do a convincing Jennifer Lawrence impression.

2. Kirsten Dunst and Jesse Plemons

Actress Kirsten Dunst used to make headlines for dating some of Hollywood’s biggest heartthrobs like Jake Gyllenhal and Garrett Hedlund as well as lovable nerds like Tobey Maguire and Adam Brody. Jesse Plemons, on the other hand, is really only known for being that guy from Breaking Bad and Friday Night Lights who kind of looks like Matt Damon if you’re stoned enough. But you know what? I’m kind of obsessed with these two together. Every millennial girl will forever associate Kirsten as head cheerleader Torrence from Bring It On, and Jesse Plemons will never not be known as lovable, nerdy second string kicker Landry from Friday Night Lights. Torrence never fared well with the popular dudes, so she found love with that alternative dude Jesse who she had that weird yet iconic, sexually charged scene with where they brush their teeth together. Let’s try to forget that less iconic pop-punk song Jesse wrote for her though, because *cringe.* And Landry was forever pining after popular bad girl Tyra, who really couldn’t make up her mind with whether she was that into him or not until she ultimately broke his heart. So Landry isn’t that sexy or cute, or really popular to boot, but it warms our cold, jaded hearts to imagine the head cheerleader and the benchwarmer getting engaged and having a baby in real life.

Kirsten Dunst

3. Diane Kruger and Norman Reedus

Joshua Jackson and Diane Kruger were that impossibly attractive hipster couple that was a match made in heaven. They’d ride Citibikes together (for fun, ew), hit up farmer’s markets for non-GMO food to support local businesses (again, for fun—why?), and go on dates to gallery exhibits (how were they not bored out of their minds?!). They didn’t get married (because again, they’re annoyingly hipster), but we always thought they were destined to be extremely good-looking and annoyingly compatible together forever. But then Diane allegedly had an affair with Walking Dead’s Norman Reedus and ended up leaving Joshua Jackson for him. Norman’s no Joshua Jackson, but he’s like, ugly hot. In a nutshell, he’s what would happen if Charlie Heaton from Stranger Things never practiced basic personal hygiene ever. I really don’t know anything about Norman, except that based off his interviews, he’s funny but he also seems like that kid in your philosophy class who would condescendingly correct other students before the professor could say anything. So Diane Kruger is attracted to eccentric guys, I guess, which makes them a decent match, and we’re excited to hate whatever outlandish name they’ll give their kid when Diane gives birth in a few months. More importantly, we like Norman and Diane together because it means Joshua Jackson is single.

4. Stassi Schroeder and Beau Clark

Stassi Schroeder is as close as we’ll get to Chanel Oberlin from Scream Queens in real life. However, just because she’s regal as fuck, doesn’t mean she always dates guys that are worthy of her. It’s like she picked all her past boyfriends straight out of the Land of Misfit Fuckboys (*glares angrily at Patrick*). Then along came Beau Clark, the alternative commercial casting and advertising associate with boyish good looks. Kristen Doute tried to set them up, but he initially nixed the idea because with her Barbie doll looks, she just wasn’t his cup of tea. They ended up meeting at an event at the Mondrian Hotel and have been together ever since. They’re kind of like Seth Cohen and Summer Roberts, if Seth had tattoos and trucker hats and Summer was blonde and never went off to Brown. What we love about Stassi and Beau together is that he’s the first of her boyfriends who seems to love how weird Stassi is. Stassi loves murder, zombies, and aliens. So Beau indulged her quirks and did a murder-themed Valentine’s Day celebration with her. It’s so great to see Stassi with a guy that has brain cells (no offense, Jax) and doesn’t treat her like shit (full offense, Frank, Jax, and Patrick). Even though we never would’ve predicted this pairing, we may think they’re even more perfect for each other than Robby and Scheana.

Stassi Schroeder

5. Audrina Patridge and Ryan Cabrera

Where were you when you learned The Hills was entirely staged? Seriously, the only couples on there that weren’t staged were Heidi and Spencer and Lauren Conrad and her headbands. So all these tabloids are saying that Audrina and Ryan are back together when, really, they were never even together to begin with. Ryan was also known for dating reality show chicks, to the point where he has more reality show credits than he does smash hit songs. (Seriously, name one Ryan Cabrera song other than “On The Way Down”.) He dated the likes of Ashlee Simpson on The Ashlee Simpson Show and Tess Taylor on Pretty Wild. Let’s face it, he was far more committed to having terrible hair than he ever was to any of these starlets. (And, based off of his Instagram, it looks like he still is.) They’re a bizarre couple because it’s pretty unorthodox that these two started off as a fake couple to deceive people only to end up falling in love for real. But then again, I feel like that’s the plot for at least a third of rom-coms from the late 90’s and early 2000’s. So Audrina and Ryan really are a reality show and movie romance come to life. We can’t wait to see these former reality stars all loved up while selling DIFF eyewear and meal replacement shakes.

Also, sidenote: loving the fact that they partied with his ex-girlfriend Ashlee Simpson-Ross recently. I guess it was a support group meeting for people who peaked in the early 2000’s. Is Mischa Barton president?

6. Elon Musk and Grimes

Who would’ve thought Elon Musk and his date would be the biggest head turners at the Met Gala? That’s not because Elon’s outfit was outrageously on theme, but because he brought goth chick Grimes as his date. Elon’s last girlfriend was Amber Heard, and his two ex-wives look like they probably run in the same social circles as Gwyneth Paltrow. So we guess he decided to pull a George Costanza and “do the opposite” by rebounding with a girl who is the antithesis of any woman he’s ever dated. And you know what? They’re pretty sweet together. They met over Twitter because they have a similar, quirky sense of humor since they’re huge nerds. Grimes has also used Twitter to defend her beau’s controversial treatment of his employees. How…romantic. Elon’s questionable ethics aside, we think this couple is pretty interesting together. Sometimes it’s nice to date someone who is not at all your type. It also kind of makes us regret outgrowing our emo phase from the 7th grade because otherwise maybe we would’ve nabbed billionaires too. Oh, well. There’s always Seeking Arrangement.

Grimes

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