10 Celeb Couples From The ’90s We Wish Would Get Back Together

For anyone who’s interested in the lives of Hollywood stars, you know that celebrity breakups can kind of hurt sometimes – even if you didn’t actually know the couple because you never actually met them. After seeing tons of cute pics of them together and hearing sweet stories, you just start rooting for them, ya know?

There are some celeb breakups that we move past quickly (like Katy and Russell – who actually thought that would last?), and some that we might just never get over… like these couples from the ’90s. Okay, fine, I get it, they’re never getting back together. But can’t a girl dream?! Check out our favorite celebrity couples from the ’90s who we wish would just get back together already.


Jennifer Lopez & P Diddy

Jennifer Lopez and P Diddy

Source: WENN

Is he still calling himself P Diddy? I don’t know. All I know is that these two were kind of perfect for each other. And look how the rest of Jennifer’s relationships turned out. I mean, okay, their breakup was less than pretty… but I just feel like these two huge superstars belong together.


Reese Witherspoon & Ryan Phillippe

Reese Witherspoon and Ryan Phillippe

Source: WENN

I know she’s married and happy and all that. I just can’t help but think that these two blonde hotties were made for each other. They even have adorable kids together! What is Ryan even doing without Reese? And have you ever seen Cruel Intentions? Watch it, and then try to tell me they’re not the cutest couple ever.


Jessica Simpson & Nick Lachey

Jessica Simpson and Nick Lachey

Source: WENN

Remember when these two had a reality show and Jessica confused tuna with chicken? Sigh. Those were the days. Yes, they both seem happy in their relationships now, but I feel like they were both so much better when they were together. And how adorable was it that Jessica waited until marriage to have sex? Nick was her true love! It’s just sad.


Madonna & Dennis Rodman

Madonna and Dennis Rodman

This might seem like a really weird pairing to everyone, and it does to me too, but that’s exactly why I want them to get back together. They’re both crazy and unpredictable and I want to know what their conversations were like.


Hilary Duff & Aaaron Carter

Hilary Duff and Aaron Carter

Okay fine, they dated in early 2000… but it still counts. Look at how freakin’ cute these two are. I couldn’t be happier for Hilary and her new baby and her husband, who I’m sure is wonderful, but this would have been like a pop dream romance come true for me. Who didn’t love Aaron Carter back in the day? Maybe Hil could have kept his career afloat if they stayed together.


Pamela Anderson & Tommy Lee

Pamela Anderson and Tommy Lee

Source: WENN

This might have been the weirdest and most terrible relationship ever, but it was also epic. Were there ever really two people more perfect for each other than these two? I just don’t think so.


Britney Spears & Justin Timberlake

Britney Spears and Justin Timberlake

Source: WENN

Remember their matching denim outfits?! That’s almost all I want to say about these two as a couple. I know that Justin is now with Jessica Biel, but I’ve just never felt like she’s right for him. I so wish Britney and Justin could have made it work – they would have been the ultimate in celeb couple royalty, and definitely would have had the cutest romance story ever.


Brandy & Usher

Brandy and Usher

To be honest, I can’t remember a ton of stuff about this relationship. But just look at their picture – they are SO cute together, and their babies would have been even cuter. Two awesome R&B singers paired together? Would have been a total powerhouse couple.


Jennifer Love Hewitt & Joey Lawrence

Jennifer Love Hewitt and Joey Lawrence

Source: WENN

I can’t tell you who either of these two are dating right now – or if they’re even dating anyone at all. If they’re both unattached, then I suggest they rekindle their old flame. It’s almost the perfect ’90s couple – Blossom meets Party of Five. Make it happen, guys!


Jennifer Aniston & Brad Pitt

Jennifer Aniston and Brad Pitt

Source: WENN

Obviously, this list would never be complete without these two on it. I’m still mourning the loss of this relationship. Yeah, I’m happy for Jen for finding herself a husband, but I will never be on board with Brad and Angelina. It’s just not going to happen.


Who was your favorite ’90s couple? Did we miss anyone? Who do you like the most from this list? Tell us in the comments!


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