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14 Couples From The '90s We’re Still Questioning (+ 6 That Were Perfect)

The '90s were full of couples that we absolutely adored but there were also a lot of couples that we couldn’t quite figure out. They seemed like oddball matches and we often wondered how they figured they were going to work considering they were so different.

We lived through the era in which we embraced the Rachel haircut and during that time we saw epic couples, such as Winona Ryder and Johnny Depp, and Brad Pitt and Jennifer Aniston. But, there were also some puzzling couples like Matthew Perry and Julia Roberts or Jennifer Aniston and Tate Donovan. Some couples seemed poorly matched until they broke up and got together with their true soulmates. These celebrities are the ones that made headlines for their relationships (and breakups) over the years.

Some of these celebrity couples have been long forgotten until now. Some of these pairings are so random that fans will question if they were really real. Did we all just imagine them? No, they are real and we are going to take a stroll down memory lane and revisit some of the best relationships, as well as some we are still questioning. Check out these 14 couples from the '90s we’re still questioning (+ 6 that were perfect).

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20 Still Questioning: David and Victoria Beckham

via Nova 969

We are still questioning how these two are still together after so many years. It’s not the longevity that puzzles us or the fact that they don’t belong together. We’re just not sure where Victoria’s infinite patience comes from. She has lived through years of media talk about her husband stepping out on her. Nothing can be confirmed, of course, but you have to ask yourself at some point whether there is some truth to all the rumors.

Victoria certainly loves her husband and is willing to stand beside him no matter what. Is that a good thing? We’re not sure there is anything that would break these two up.

19 Still Questioning: Justin Timberlake and Britney Spears

via In Touch Weekly

Back in the '90s we saw Britney Spears and Justin Timberlake get together and it seemed just too perfect. They were both popular pop stars that met when they were just kids on the Mickey Mouse Club. We wanted to see them get married and live happily ever after. But then they broke up because Britney saw something shinier and she went after it.

Timberlake was so sad that he wrote a song about it and that was the end of the pop duo. We are questioning their breakup more than anything but they were both quite young at the time and dealing with massive fame.

18 Still Questioning: P. Diddy and Jennifer Lopez

via 92 Q

Diddy and Jennifer Lopez were an odd match from the beginning even though fans loved seeing them together. Sure, she was “Jenny From The Block” but she wasn’t anywhere near as hardcore as her boyfriend who kept getting in trouble with the law. The two were reunited at a show at Planet Hollywood in Las Vegas where she sang to him in the audience.

“Jennifer saw Diddy in the crowd and sang to him. She seemed to be performing with a wink and a nod to him. At one point, she shouted out Diddy's name so the entire audience knew he was there,” a source told Daily Mail.

17 Still Together: Sarah Michelle Gellar and Freddie Prinze Jr.

via People

These two are a perfect pairing from the '90s and we can’t believe that they are still together. They met on the set of I Know What You Did Last Summer and they have been together ever since. They made the choice to leave Hollywood and raise their children out of the spotlight which is probably part of why they are still together.

Gellar told Us magazine that communication is key in their marriage. “Communicate. That’s the key. It’s about being present,” she said. “Listening is the most important thing.” Prinze Jr., however, told Us, “We still make each other laugh. And we treat each other with respect.”

16 Still Questioning: Bruce Willis and Demi Moore

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At first, we thought that these two were a match made in Hollywood. They were both big actors in the '90s and together they were a power couple. But there was a lot of strangeness that went on in their marriage as well as with Demi trying to be the perfect wife.

She once hired a dancer for Bruce Willis’ birthday party and the dancer could have been her twin. It was just after she had made the movie Striptease and many fans questioned why she would do something like that. It wasn’t long before the two were calling it quits in Hollywood.

15 Still Questioning: Jennifer Aniston and Tate Donovan

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Jennifer Aniston and Tate Donovan didn’t meet on her popular TV series Friends. They had been dating for two years prior to that and were actually breaking up just as he got on the show. Sure, they were cute onscreen but we really didn’t get them as a real-life couple.

You may have wondered why he was only on the show for a short period of time. “It was just six episodes. I mean, only because we were breaking up. We were like, ‘Hey, can we not keep doing this? 'Cause this is really painful and tough,’” he recalls of his and Aniston’s feelings about working together at the time, as Fame10 reports. “The people that know that we dated think that we met on Friends. But in fact, we had dated for two years before then, and it was over by the time we were on Friends together.” Ouch!

14 Still Questioning: Matt Damon and Minnie Driver

via People

When these two got together it was definitely puzzling. They just seemed so different from each other. They were a couple in the movie Good Will Hunting and that transferred over into real life. The two were together for a couple of years and then Matt Damon went on Oprah and told the host that he and Driver weren’t together anymore and that was how she found out that they had broken up.

Driver told Los Angeles Times, “It’s unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically [out of place]. Of course, he was busy declaring his love for me on David Letterman a month previously.”

13 Still Questioning: Ben Affleck and Gwyneth Paltrow

via Fox News

We could never really understand why Ben Affleck and Gwyneth Paltrow got together, especially since she was just out of a broken engagement with Brad Pitt. Affleck is a great catch but he’s no Brad Pitt.

Paltrow made it pretty clear on the Howard Stern Show that she had no intention of ever marrying Affleck. “It’s interesting, I think [there are] certain boyfriends where you are trying to work stuff out, right? Like, you’re trying to heal certain stuff from your childhood, and he was very much a lesson in that way.” We’re sure he was really happy to hear that, Gwen.

12 Perfect Together: Johnny Depp and Winona Ryder

via InStyle

Johnny Depp and Winona Ryder were one of the steamiest couples of the '90s and we really thought that they would make it. They seemed so in love but Depp may have cursed them when he decided to get “Winona Forever” tattooed on his arm. The two were engaged to be married and Ryder said she became depressed after breaking off the engagement.

“I had just done Dracula and Edward Scissorhands. I had just had my first real break-up, the first heartbreak,” she told Elle. She says she “was very depressed after breaking off my engagement with Johnny. I was embarrassingly dramatic at the time, but you have to remember I was only 19 years old.”

11 Still Questioning: Kurt Cobain and Courtney Love

via Famous Biographies

Many people thought this rocker couple was a match made in heaven but there were others that knew what was really going on in the relationship and saw some serious red flags.

“Courtney and Kurt are the nineties, much more talented version of Sid and Nancy,” a record executive once noted, as Biography reports. “[Courtney's] going to be famous and [Kurt] already is, but unless something happens, they’re going to self-destruct. I know they’re both going to be big stars. I just don’t want to be a part of it.”

Their love certainly did end badly.

10 Perfect Together: Jennifer Aniston and Brad Pitt

via StyleCaster

They were the golden couple of the '90s and it was heartbreaking to see them break up. What seemed like the perfect coupling disappeared after Pitt finished filming Mr. & Mrs. Smith. There are just some things that a relationship can’t survive.

The two have since forgiven each other for the past and Pitt even attended Aniston's birthday party this year. "Brad wishes he’d handled the end of their marriage in a more thoughtful manner," a source told Elle.

Aniston, in an interview with Vanity Fair after the split, famously said of Pitt, "There’s a sensitivity chip that’s missing."

9 Still Questioning: Brad Pitt and Gwyneth Paltrow

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We couldn’t figure out why these two were ever together, especially after we saw how perfect things were between him and Jennifer Aniston. Paltrow explained to Vanity Fair why the two broke up.

“I was such a kid,” she shared. “I was 22 when we met. It's taken me until 40 to get my head out of my (…). You can't make that decision when you're 22 years old . . . I wasn't ready, and he was too good for me . . . I didn't know what I was doing.” She actually just decided to leave the perfect man. It was Brad Pitt!

8 Still Questioning: Matthew Perry and Julia Roberts

via New York Post

There were a lot of huge stars that guest-starred on Friends over the years and Julia Roberts was one of them. She and Matthew Perry played a couple on the show and decided to take that into real life.

Matthew Perry must have thought he won the lottery when the two of them started dating. She was a megastar at the time and, well, he was Matthew Perry. The two didn’t last very long, which no one in the world was surprised about. The two went on a bunch of dates but the relationship (if it was even one) fizzled out.

7 Still Questioning: Ryan Reynolds and Kristen Johnston

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We had completely forgotten about these two and it’s no wonder because it makes absolutely no sense. How did they even meet? They probably both were on the same level of fame during the '90s which is to say that neither of them was that famous.

But still, we are surprised that Ryan Reynolds dated her. They seemed completely different. We questioned this relationship from the beginning but it only lasted a couple of months before they called it quits in 1999. It was definitely a weird year for Hollywood romances and this one topped it!

6 Still Questioning: Richard Gere and Cindy Crawford

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Richard Gere snagged himself a world-famous supermodel, Cindy Crawford, and it still has us shaking our heads in confusion. In the '90s they were one of the most famous couples to walk the red carpet and they definitely looked good together. It may have been the 17-year age difference that finally ended their four-year marriage.

Crawford told Marc Maron’s WTF podcast that she had been too young to truly fall in love. “And then, as I started kind of growing up and growing into myself—it’s hard to change the nature of a relationship once you’re already in it,” she said.

5 Perfect Together: Reese Witherspoon and Ryan Phillippe

via Life & Style

These two met on the set of Cruel Intentions and it was practically like love at first sight. He showed up to her birthday party that year and she famously stated, “Are you my birthday present?” and that was all it took for the couple to get together.

They really seemed like they were two actors who were going to make it. They married, had two children and then things fell apart after Phillippe stepped out with a costar. They're just one of those couples that you remember sadly because they were adorable together and were obviously once very much in love.

4 Still Questioning: Courteney Cox and Michael Keaton

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We were surprised when these two got together because he was a huge movie star and she was just coming into fame during the TV series Friends. But they did make a cute couple. They became one of the most famous couples of the 90s and it was hard for them to keep any privacy in their relationship because the paparazzi were all over them.

They were together for six years before they broke up in 1995. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” Cox told People.

3 Perfect Together: Will Smith and Jada Smith

via WDKX.com

It’s a pretty big deal when a Hollywood couple can say that they have been together for over 20 years. It’s almost unheard of in the industry. It may have a lot to do with the fact that Will Smith treats his wife like the Queen that she is.

"Just like in my house when I was growing up, I knew that my mother was the center," he shared to People. "If Mommy is straight, then everybody else will be. I am very clear at home that Jada’s physical, mental, spiritual health and comfort comes first." How incredible is that?

2 Still Questioning: Emilio Estevez and Paula Abdul

via Today Show

It’s true, these two were a couple in the '90s and they even got married. They got married a year after they met but then were divorced just two years later. Emilio Estevez had already been married once before and had two children from that marriage. Abdul stated that their marriage ended because he didn’t want more children and she did.

“It was very hard for him to admit that he couldn’t handle having kids again,” Abdul told EW. “It was heartbreaking for us both.”

Maybe that should have been a conversation they had before they got married.

1 Perfect Together: Tom Cruise and Nicole Kidman

via Scribol.com

When these two met on the set of Days of Thunder it was like fireworks went off. They were a sizzling couple that got together and married each other. They certainly made an impression every time that they hit the red carpet together.

It was practically love at first sight for Kidman who was heartbroken by the end of their marriage. She told Vanity Fair about the first time that she laid eyes on Tom, saying, “I remember being so nervous and seeing Tom Cruise drive up in a Porsche . . . He got out of the car and walked through the door, and I was like, ‘Ah.’”

Sources: Daily Mail, Us, Fame10, Elle, Biography, Vanity Fair, People

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