Wait—They Dated? 10 Past Couples You Forgot Were Together

Hollywood couplings change like the weather. Do you remember if it was raining on this day in 1995? Yeah, me neither. So, it’s totally understandable if some of the most unlikely Hollywood pairings didn’t stick in your memory. Here are some of the most unexpected celebrity couples you’ve probably forgotten about.

Courteney Cox And Michael Keaton

Courteney Cox (L) in dark blue dress with Michael Keaton, who is wearing a black suit and bowtie
(Photo by Diane Freed)

Sitcom darling Courteney Cox and Batman star Michael Keaton met in 1989. The kindred spirits were extremely private, making only a handful of public appearances together during their five-year-long relationship. Their first date took place at Cox’s house where she and Keaton reportedly talked for hours about their dream homes. When they split in 1995, Cox told People that she still loved him, but that relationships were complicated.

Owen Wilson And Sheryl Crow

Sheryl Crow (L) in black shirt standing next to Owen Wilson, who is in a blue button-down shirt with sunglasses
(Photo by Vince Bucci/Getty Images)

The Royal Tenenbaums actor met the “Soak Up The Sun” songstress in 1999 when she made her acting debut in Wilson’s The Minus Man, a serial killer flick that you’ve also probably forgotten about. They dated for two years before calling things off in 2001. Crow later admitted in the liner notes of her 2002 album C’mon, C’mon, that her song “Safe and Sound” was about her and Wilson’s romance.

Christina Applegate And Brad Pitt

Split Image (L): Christina Applegate in white dress with black detail

(R): Brad Pitt wearing all black suit
(Gregg DeGuire via Getty Images/Ovidiu Hrubaru/shutterstock.com)

As it turns out, Jennifer Aniston was not the only Green sister Brad Pitt ever had eyes for. Christina Applegate dated the Fight Club actor in 1989, but little is known about their brief time together. The young couple attended the MTV Movie Awards together that same year, but legend has it that Applegate ditched Pitt for another man before the night was over. No one knows who pulled Applegate away from the rising star, but we do know that it spelled the end of their brief fling.

Matthew McConaughey And Sandra Bullock

Sandra Bullock (L) in black dress sitting next to Matthew McConaughey, who is wearing a black  blazer over a white dress shirt
(Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images)

This unlikely pair hit it off on the set of A Time to Kill in 1996. The private couple kept things quiet for their two-year-long romance before ultimately calling it quits. They both went on to marry other people and have children, but rumor has it they stayed good friends. Bullock has even been spotted socializing with McConaughey’s wife,  Camila Alves.

Neil Patrick Harris And Christine Taylor

Split image (L) Neil Patrick Harris wearing black suit (R): Christina Taylor in bleu tube top and black jeans

Former child actor Neil Patrick Harris didn’t come out of the closet until 2006, and he certainly dated a few of Hollywood’s most eligible bachelorettes before coming to terms with his sexuality. Harris dated actress Christine Taylor from 1997 to 1998, and he even credits her with helping him accept himself. “She’s the coolest, nicest chick ever. She’s an absolute catch, and I thought, ‘If I’m not going to feel the super sparks with her… it probably means I’m gay,” he told Howard Stern in 2008.

Dean Cain And Brooke Shields

(L): Dean Cain in black suit over white dress shirt
(R): Brooke Shields in black jumpsuit
(Joe Seer/Fred Duval/shutterstock.com)

Shields and Cain were the picture of young love after meeting in 1983 at Princeton University. They went on to date for their entire college careers before ultimately calling it quits in 1987. In her memoir, Shields recalls her overbearing mother playing a part in their breakup. Cain remembers his college sweetheart fondly, telling Today in 2014, “We were in love. She was a wonderful girl.”

Uma Thurman And Gary Oldman

(L): Gary Oldman in black suit and bow tie 
(R): Uma Thurman on red carpet in white gown
(Featureflash Photo Agency/shutterstock.com)

This forgotten couple didn’t just date, they actually ended up tying the knot. The unlikely pair started dating somewhere around 1989, but the early details of their relationship remain a mystery. Thurman was 18 when she fell head over heels for the Academy Award-winning actor. They got married in 1990 but divorced less than two years later. While they haven’t breathed a bad word about each other in the press, they have both expressed that their marriage was a mistake.

Lance Bass And Danielle Fishel

(L): Lance Bass in green velvet suit 
(R): Danielle Fishel in floral patterned dress
(Kathy Hutchins/shutterstock.com)

If you were a teen in the late ’90s, you might remember that Boy Meets World star Danielle Fishel once dated NSYNC member Lance Bass. The young couple’s romance lasted about a year, and Bass even took Fishel to her high school prom. However, Bass remembers that night as a pivotal moment in his journey to discovering his sexuality. After Bass officially came out in 2006, he and Fishel reconnected as friends. Now, the former couple is working on a movie based on their relationship.

Chris O’Donnell And Reese Witherspoon

(L): Chris o
(Featureflash Photo Agency/lev radin/shutterstock.com)

If you don’t remember O’Donnell and Witherspoon’s brief maybe-romance, we don’t blame you. The pair first sent tongues wagging in 1993 after they attended a tribute party for Al Pacino together. However, Witherspoon was only 16 at the time while O’Donnell was 22, and neither star ever confirmed their relationship. There’s still a possibility that they never actually dated, but, either way, it’s clear this pairing wasn’t meant to be.

Ashton Kutcher And January Jones

Ashton Kutcher (L) in all-black suit with his arm around January Jones, who is wearing a silver blazer
(Photo by Newsmakers)

Our last forgotten relic of Hollywood dating trivia is Ashton Kutcher and January Jones. This seemingly random pair actually dated at the very start of their respective careers, and they were living together when Kutcher got his big break on That ’70s Show in 2000. Jones has alluded that they didn’t end on the best of terms in 2001 after 3 years of dating, but it’s clear their careers and personal lives recovered quite well from the ill-fated relationship.

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