Sometimes it seems like everybody in Hollywood has dated, to the point where it feels kind of incestuous. Never is that feeling more present than when you learn that two celebrities you would never have put together were once a couple — or at least an “item,” whatever that means. It’s especially weird when you learn that they were together for years. This is different from remembering that Kirsten Dunst and Jake Gyllenhaal used to go out or that J.Lo and Diddy were a thing. These are the kinds of celebrity couples that make you go, “Wait… what? Them? When? For that long? Where was I? Why haven’t I heard this?” Unless you’re a devoted fan of these people, odds are you had no idea they went out. Or maybe you’re a genius and you remember all of them, in which case please teach me your powers of memorization. There’s a Shakespearean monologue I’ve been trying to remember for no reason.
1. Rachael Leigh Cook and Shane West
Talk about the ultimate teen movie mash-up! Rachel and Shane dated from 1997 to 1999, aka the best year for movies ever. I guess the late nineties movie magic was just too much for their young romance to handle.
2. Gwyneth Paltrow and Luke Wilson
You might have loved these two as a kind of incestuous pair in The Royal Tenenbaums. But did you know they were also a couple off-screen? They dated for about a year between 2001 and 2002, and soon after that our Gwynnie got engaged to Chris Martin. The rest is Appley, Mosesy history. I wonder if she ever made him eat kale.
3. Kristen Bell and Matthew Morrison
(Photo: Getty Images for UNICEF)
Maybe it’s because he plays a teacher on Glee, but I always assumed Matthew Morrison was a good bit older than Kristen Bell. Turns out they’re only a year or so apart, and they went to college together at NYU’s Tisch School of the Arts. It looks like they’re still on good terms, based on the photo above and the fact that Kristen still refers to him as “Matty” and says he’s her favorite part of Glee.
4. Tobey Maguire and Rashida Jones
This pairing totally blew my mind, not only because I would have never put them together but because they were together for about three years in the late ’90s. That’s no casual fling. I guess it makes sense that they flew under the radar since Rashida wasn’t a big star then, but wowzers, this one really surprised me.
5. Lisa Kudrow and Conan O’Brien
Talk about a funny couple! These two dated when they were wee improv students, but Lisa says they ended up being “better as friends.” She also credits Conan with encouraging her to stick to improv when she considered quitting, and that led her to become a member of the Groundlings. I think these two seem swell.
6. Zooey Deschanel and Jason Schwartzman
(Photo: Getty Images)
Before Zooey Deschanel was the adorkable star of New Girl, she was quirking it up with Jason Schwartzman. Their relationship lasted for about two years from 2003 to 2005. Just look at them sticking their faces together like two vintage dolls. I can totally see how these two were a thing. They probably shopped at vintage record stores and ate vegan cupcakes together.
7. Sofia Vergara and Enrique Iglesias
Um, can you say hot hot hot? These two were an item in the ’90s, and before Sofia made it big on Modern Family she was often known as “Enrique’s ex.” And now here we are going, “Did you know they dated? I didn’t know they dated.” What a world!
8. Kieran Culkin and Emma Stone
I think I just assume that Emma and Andrew Garfield have always been together and will be forever and ever until the end of time, so hearing about her relationship with Kieran boggles my mind. These two co-starred in 2009′s Paper Man and stepped out as a couple in 2010. They broke up in 2011, and soon after that Andrew came swinging into Emma’s life and hasn’t left since. They teamed up again for this year’s Movie 43.
9. Amanda Seyfried and Ryan Phillippe
This happened? Was I just not paying attention? Apparently these two, who are eleven years apart, met at Kate Hudson’s Halloween party in 2010 (no word on if Amanda was dressed as a sexy mouse), and they were off and on for seven months after that. Later Amanda blamed their relationship for anxiety attacks and vowed to avoid dating celebrities. We know how that turned out.
10. Matt Damon and Winona Ryder
Holy what in the world on a cracker! Gwyneth Paltrow introduced these two in 1997, but they broke up a few months later. There doesn’t seem to be any bad blood between them, though, since Winona said in a 2009 interview, “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.”
11. Emma Roberts and Alex Pettyfer
Maybe I’m just not in tune enough with the romantic behavior of Hollywood’s youth, but this one surprised me. They co-starred in the classic 2008 movie Wild Child. Alex even went as far as to tattoo Emma’s initials on his finger. Emma later commented in an interview after their break-up that girls should “not date a model. Ever.” Uh oh.
12. Nick Cannon and Kim Kardashian
This one might have been stored somewhere way back in the dark recesses of my mental celebrity relationship vault, but it’s been gathering dust for a long time, and for some reason seeing them in a picture together feels weird. Before Nick was married to Mariah Carey and Kim was taking over the world one directionally named baby at a time, these two dated from September 2006 to January 2007. Nick later revealed that the reason they broke up was because Kim told him her sex tape didn’t exist. And we all know what a big fat lie that was.
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