Hugh Grant & Elizabeth Hurley, & More '90s Celebrity Couples Who Should Totally Get Back Together

Some '90s celebrity couples are best left in that decade. As much as I adore them as individuals, Britney Spears and Justin Timberlake were only perfect in their particular time and place, and parted ways for very good reasons. Jennifer Aniston and Brad Pitt? Both so pretty it hurts, but hallelujah, was their breakup the best thing to happen to them both. The same can't be said for iconic '90s couples like Hugh Grant and Elizabeth Hurley. The two were spotted together on Sept. 10, 15 years after splitting up, possibly proving that love sometimes waits — even if takes more than a decade for the two people in question to get their act together and realize they were meant to be.

Sometimes people split up and they continue to marvel about the other's brilliance to the media. In those cases, you can't help but think that their breakup was an unfortunate mistake and that they'll come to their senses one day and find their way back to one another. Other times, you get the sense one party would totally make a go at a relationship again if both were single or he/she hadn't mucked things up so badly the first time around.

These six '90s couples parted amicably and have said such lovely things about one another that you can't help but think it's totally plausible they'll shock the world and reunite one day.

1. Hugh Grant & Elizabeth Hurley

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Admittedly, I'm jumping the gun with Grant and Hurley, who have yet to comment on whether the aforementioned outing was a friendly one or something more. It should be noted that both have admitted they remained best friends, even after Grant was arrested for "lewd behavior" with sex worker Divine Brown in 1995 (yes, while the two were dating). The actor is even godfather to Hurley's 13-year-old son and the former model and actress has said he's like family to her. Yeah, yeah, that's all well and good, but it when two people seem to like each other as much as they do — and have a romantic history together – you can't help but wonder... hmm, what if?

Here's what Hurley told Access Hollywood about Grant back in March: "I mean, there wasn't a question of us not being best friends. I think when you've been with someone for a long time, they are family. And to me, he's like a big brother. Or not even a big brother, 'cause sometimes I'm more grown up than him. But we're like siblings now." Uh huh.

2. Angelina Jolie & Billy Bob Thornton


Angelina Jolie and Billy Bob Thornton were married for three years before their 2003 divorce — but, hey, they dated in the '90s which, technically, gives them '90s couple cred. They reportedly split because Thornton didn't want kids and Jolie kind of said, oops, too bad and adopted her son Maddox. But there's absolutely no love lost between the two. Thornton told The Hollywood Reporter, "We had a great time together. We had a great marriage and I chickened out because I didn't feel good enough. That's all that happened. It was no big deal, we never hated each other."

Jolie wrote the forward to her ex's book and dedicated it to a man who has a "big beautiful heart." So, yeah, basically, if things don't work out between Jolie and Brad Pitt (and I'm not wishing that upon them), I'm betting Thornton will come calling. But who wouldn't?

3. Gwyneth Paltrow & Brad Pitt


Did you think I was going to try and fake hook up Angie without doing the same for Brad? Gwyneth Paltrow was just 22 when she and Pitt met on the set of Seven and began dating in 1995. They were so in love that they got engaged, but only stayed together for three years because, as Paltrow told Howard Stern, she was young and foolish and Pitt was "too good" for her back then. I'm going to take that to mean he was better equipped to handle a long-term commitment. Here's what she had to say about him, as reported by Vanity Fair

I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt. My father was so devastated when we broke up. My father loved him like a son. I was such a kid. I was 22 when we met. It's taken me until 40 to get my head out of my ass. 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.

Pitt hasn't been quite as forthcoming with his feelings about Paltrow, but there's little doubt in my mind that both don't think about one another every now and then.

4. Kate Moss & Johnny Depp


Kate Moss is reportedly divorcing Jamie Hince and Johnny Depp is happily married to Amber Heard, so this is a reunion that isn't likely to happen anytime soon. But Moss and Depp were the "it" couple of the 1990s and for good reason: neither could possibly find another soul who was as hip as either one of them. Looking back at their time together, Moss told Vanity Fair,

There’s nobody that’s ever really been able to take care of me. Johnny did for a bit. I believed what he said. Like if I said, "What do I do?," he’d tell me. And that’s what I missed when I left. I really lost that gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!

I doubt I'm alone in thinking he was the one who got away for her. Depp is, obviously, too cool for school and wouldn't possibly comment on Moss, but the world has become pretty used to the idea that he's a mystery wrapped in an enigma — which is just Moss' type.

5. Ben Affleck & Jennifer Lopez

Ben-Ari Finegold/Getty Images Entertainment/Getty Images

Technically, Jennifer Lopez and Ben Affleck are an early '00s couple. And, let me be clear: I think Affleck needs to take some time before he settles down with another woman, but I really think he and J. Lo could work. When they broke up, the singer and actress told VH1, "I don't think I had ever been heartbroken in that way before. I had so many hopes and dreams on something." Affleck has said he respects Lopez and checks in with her to congratulate her on wise career moves (he counts American Idol as one). "We don't have the kind of relationship where she relies on me for advice," he told GQ. "But we do have the kind of relationship where there'll be an email saying, 'Oh, your movie looks great." I remember when she got American Idol, I said, 'This was really smart. Good luck.'"

What does Lopez remember? Dressing Affleck: "I did, kind of like, say, 'You're a movie star! You should wear a suit. You should do this with your hair.' For sure!" Lopez said on Watch What Happens Live!

6. Hillary Duff & Aaron Carter

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Again, I'm taking liberties here because Aaron Carter and Hillary Duff dated in 2000 — and would have possibly continued dating if Carter hadn't taken up with Lindsay Lohan. Now that Duff is separated from husband Mike Comrie and Carter has professed his undying love to her via social media (which I admit was awkward as hell), I can't help but wonder what would happen if these two reunited for a friendly drink. In 2012, after learning about Duff's marriage, Carter told Fox News: "I'm really happy for her that she's in a successful relationship and that she's going to have a baby. Sometimes I think to myself, maybe that could have been me but it is what it is." And then, of course, there was this tweet:

Duff reportedly thinks there's something a little strange about all of his sudden tributes, but if she's ever game to recreate the (not quite) '90s, I'm guessing Carter will be right there at her door.

Now, if all of the stars could align so we could see all of these couples reunite at the same time, many celeb relationship goals will finally be recognized.