18 Celebrity Couples That Fizzled Out Way Too Soon

NEW YORK, NY - JANUARY 06: Nicole Kidman Visits 'The Tonight Show Starring Jimmy Fallon' at Rockefeller Center on January 6, 2015 in New York City. (Photo by Theo Wargo/NBC/Getty Images for 'The Tonight Show Starring Jimmy Fallon')
Source: Theo Wargo/NBC/Getty Images Entertainment/Getty Images

Everyone's had a "meh" first date or two, and celebrities are no different. While tabloids may focus on steamy-hot celebrity affairs or longterm power couples, there are plenty of stars who got together — and broke things off — without any drama. While we may have heard of these stars hooking up, they didn't exactly make a love connection. So what celebrities could have been a thing, if the stars aligned a tad differently? Click through to find out. 

Nicole Kidman

The Moulin Rouge actress could have dated this late night host. 

Jimmy Fallon

Kidman went on The Tonight Show Starring Jimmy Fallon and admitted to the host that she used to have a bit of a crush on him — but that he blew it by playing video games when they were hanging out!

Blake Lively

When Lively was spotted out and about this A-List actor, the entire internet was abuzz with reports on this “new celebrity couple.”

Leonardo DiCaprio

The couple was spotted hanging out together in France, but the relationship — if that’s what it was — fizzled almost as quickly as it started. Lively has claimed that she spent most of her time in France studying the language, so it’s possible that these two were never really an item in the first place. 

Lea Michele

Though she played his student on GleeMichele admitted that she used to date this co-star. 

Matthew Morrison

Yep, Schue and Rachel dated — at least, very briefly. Michele confessed in her memoir Brunette Ambition that she went on a couple of dates with Morrison back in their Broadway days. 

Leonardo DiCaprio

The single celebrity was bound to make this list more than once. 


Rumor has it that these two spent the night hooking up at a recent Hollywood bash.


The media mogul admitted that she had a brief fling with this famous film critic. 

Roger Ebert

Back in the ’80s, the now-late critic Ebert took Oprah out on two dates. 

Amy Poehler

The Parks and Rec actress is one lucky gal. 

John Stamos

According to Poehler, she went on a “maybe-date” with Stamos years earlier, but things never went further than that.

Liam Neeson

This actor was actually sort of serious with his younger co-star. 

Julia Roberts

Back in the day, these two actually did date — they just failed to take the next step. The 19-year-old Roberts began dating Neeson (16 years her senior) after they filmed Satisfaction together.

Melissa Joan Hart

The Melissa & Joey star admitted that she achieved the ’90s girl dream of making out with this boy bander. 

Nick Carter

Hart told Access Hollywood Live that she hooked up with this Backstreet Boy cutie back in the day. 

Chelsea Handler

Handler briefly dated this rapper after interviewing him on her show. 

50 Cent

Though the couple fizzled out quickly, 50 Cent has stated that he’s “still friends” with the Chelsea Lately host. 

Katie Couric

Couric revealed that she went on a very awkward date with this talk show host. 

Larry King

Couric stated that she went on a date with King back when they were both living in Washington, D.C. The television host said that King eventually took her back to his place, where Couric announced that she’d prefer to date someone closer to her own age. 


This pop star went on a date with this member of ‘N SYNC. 

Joey Fatone

According to Pink, Fatone was “in love” with her when they toured together early in their careers, and even took her on a date to Friendly’s.


Before romancing his now ex-wife Heidi Klum, Seal was briefly with this other supermodel. 

Tyra Banks

The America’s Next Top Model host dated Seal for a brief period of time in 1996. 

Matthew Perry

The former Chandler Bing almost dated this Hangover actress.

Heather Graham

Perry and Graham got together briefly in 2003, but their relationship fizzled quickly. 

Seth MacFarlane

The Family Guy creator was briefly tied to this young actress. 

Amanda Bynes

The Easy A actress was tied to the comedian back in 2008, when they were spotted out together. Things appeared to taper off after that. 

Kim Kardashian

Before she was a crazy-famous reality star, Kardashian went on a date with this celeb. 

Nick Lachey

The former 98 Degrees band member doesn’t have fond memories of his last date with Kardashian, whom he alleges called the paparazzi to come meet them at the movie theater. 

Winona Ryder

The Black Swan actress spent some time with this funny man in the early ’00s. 

Jimmy Fallon

Fallon again! These two were spotted out together in 2002, but nothing ever seemed to blossom, romance-wise. Ryder later told W Magazine that they were “just friends.” 

Taylor Swift

Swift liked this musician so much that she wrote the song “Enchanted” about meeting him. 

Adam Young

The man behind Owl City and the 1989 mogul hit it off when they met and exchanged e-mails for a while, but a real romance just never blossomed between them. 

Drew Barrymore

The Blended actress never called this leading man again after their one date. 

Christian Bale

According to Bale, he took Barrymore to see a horror movie back when they were teenagers, but that date was the end of it — she never called him again!

Brad Pitt

The World War Z actor was ditched by this Anchorman actress when they were teenagers. 

Christina Applegate

Applegate allegedly took her good friend Pitt as her date to the MTV Movie Awards in 1989, but left him there and went home with another guy! The actress admits that she still feels bad about that one.