10 Mind-Blowingly Random Celebrity Couples

By Emily Richardson | Celebrity | November 29, 2023 |

By Emily Richardson | Celebrity | November 29, 2023 |

Over the weekend, this tweet about random celebrity couples went viral:

that one random celeb relationship that everyone moved on from but you literally cant forget it and think about it every day

— ؘ (@dayasgalore) November 25, 2023

The comments are fun, but, unfortunately, many of the couples mentioned were, well, not that random. Zendaya and Jacob Elordi? They’re both ridiculously good looking and acted together in Euphoria. Miley Cyrus and Nick Jonas? Disney tweens hooking up is a no-brainer. Emma Stone and Andrew Garfield? OK, I can see why people wouldn’t want to move on from that very special moment in history, but, again, there’s nothing weird about Spider-Man stars dating (see: Tobey Maguire and Kirsten Dunst, Zendaya and Tom Holland).

So, let’s right Twitter’s wrongs and discuss ten truly random celebrity couples. Some I knew, some I didn’t know, some I must’ve known at one time but I probably buried the info deep, deep inside my brain…

Seth McFarlane and Emilia Clarke

I’m going to be very real with you. Way back in the mid-2000s, when I was in college, I had a mild crush on Seth McFarlane. I know. Please know I am deeply ashamed. Then there’s poor Emilia Clarke, who actually dated Seth in 2012. She was 26, he was 39. They broke up the following March. According to a source, the couple just couldn’t get over the long-distance thing; Seth was based in California and Emilia was over in Europe filming Game of Thrones. So, in a way, Daenerys Targaryen saved Emilia from Seth McFarlane. Almost makes up for the whole “burning King’s Landing to the ground” thing.

Ashley Olsen and Lance Armstrong

Heh? Apparently, back in 2007, 36-year-old Lance Armstrong briefly dated 21-year-old Ashley Olsen (as you can already tell, age gaps are a common theme on this list). According to Juliet Macur’s book Cycle of Lies: The Fall of Lance Armstrong, Lance’s friend “warned” him “that his May-December romance could damage his cancer work.” Lance’s response? “She’s 21… F—- you!” As we all know, Ashley wasn’t the one to “damage” Lance’s reputation as the king of charity; he did that all on his own.

Naya Rivera and David Spade

Naya Rivera and David Spade showed off some PDA in the pool and that's what we missed on Glee. https://t.co/LPGSk0yEiN pic.twitter.com/T13wAoCdOx

— E! News (@enews) April 3, 2017

Was Cupid drunk when he matched David Spade and the late, great Naya Rivera? We may never know. These two dated for a few months in 2017, when Naya was 30 and David was 52. That January, paps caught them grabbing dinner together in LA. In March, they were photographed canoodling in a pool at a Hawaiian resort (Adam Sandler and Rob Schneider were also on the trip). Alas, their love was not meant to be. By June, Spaya was through.

Serena Williams and Brett Ratner

I audibly gasped at this one. Serena Williams, the greatest athlete of all time, dated Brett Ratner? Disgraced creep/director/producer Brett Ratner? Yep. They were together from 2004 to 2005; Serena was 23ish, Brett was in his mid-thirties. This is a disgusting piece of information, and I’m so happy Serena escaped and found love with her Reddit husband. He seems nice.

Glenn Close and Woody Harrelson

Apparently, Glenn Close and Woody Harrelson dated for five months in 1991. Even though they’re both actors and likely ran in the same circles, this coupling is still very strange to me. Is it because Glenn is 15 years Woody’s senior? Is it the fact that Glenn was a “very serious actress”, and, at the time, Woody was just Woody from Cheers? Or am I simply thrown by their oh-so-’90s-fashion in the above pic?

Carmen Electra and Simon Cowell

I don’t have strong feelings about this one, but it is indeed random. Carmen Electra dated Simon Cowell for a few months in 2012. According to gossip legend, things ended when Carmen walked in on Simon in bed with his now-wife, Lauren Silverman. Fun fact: Lauren was married to another man at the time. Oopsies! In 2013, Lauren’s then-husband filed for an at-fault divorce, citing his wife’s affair with Simon. Later that year, Carmen was linked to Ryan Lochte. Ahhh, the cosmic shuffle of Hollywood love.

Cher and Tom Cruise

Cher and Tom Cruise: a random couple for the ages. These two met at Madonna and Sean Penn’s wedding in 1985 and began dating later that year. Cher was 39, Tom was 23. Cher has said she ranks Tom as one of her top five greatest lovers, which… huh. I didn’t expect that. The pair have remained friends in the years since, but Cher admits she doesn’t “get” Tom’s “whole Scientology thing”: “I can’t understand it so I just… don’t.”

Steve Martin and Anne Heche

Steve Martin’s dating history is pretty wild. For example, he dated Karen Carpenter, Mary Tyler Moore, Kristin Davis, and Anne Heche, who passed away last year. Steve and Anne dated from 1994 to 1997. Steve was 24 years Anne’s senior, and she eventually dumped him. In an interview, Anne said there wasn’t anything wrong with Steve, “it was just that it was not what I wanted to commit my life to.” The next year, she moved on to Ellen DeGeneres. As for Steve, he married another Anne, writer/Tina Fey look-a-like Anne Stringfield, in 2007. Anne #2 was 27 years his junior, and gave birth to their only daughter in 2012. Steve was 67.

Bethenny Frankel and Eric Stonestreet

I’m sorry, but what the actual hell? As a Real Housewives obsessive, I’m flabbergasted that I didn’t know about Bethenny Frankel and Eric Stonestreet’s short-lived 2015 romance. In 2016, the pair appeared on Watch What Happens Live and kinda-sorta admitted they used to be an item. Eric said, “We met, and I think we both decided we make much better friends… but she’s a wonderful kisser!” Here’s the clip:

Bill Murray and Kelis

Bill Murray and Kelis have broken up, according to Page Six. pic.twitter.com/sfASgPduFL

— Pop Crave (@PopCrave) August 25, 2023

Finally, Bill Murray and Kelis. These two dated this year. Rumors began a-swirlin’ in June, after 72-year-old Bill was spotted at multiple Kelis concerts. By August, they were dunzo. According to a source, 44-year-old Kelis ended things with Bill because “things just ran their course.” A real fever dream of a relationship.