Ryan Gosling & Rachel McAdams Plus 16 More Celebrity Couples We're Still Mourning the Loss Of

I am totally guilty of shipping celebrity couples. Yes, I am fully aware that celebrity couples are real people capable of making their own decisions in the love department, but that doesn't mean that I'm not bummed when a celebrity couple that I found just plain adorable calls it quits. There are a ton of former celebrity couples who broke my heart when they broke up, whether it was because they were too cute for words or because they were so wacky together, they fascinated me with their union. Here are 17 celebrity couples who have split, and left me reeling.

by Kaitlin Reilly

Justin Timberlake & Britney Spears

This pair ruled the pop music scene in the late ’90s and early ’00s. If you didn’t ship Britney and Justin, you were totally a Backstreet Boys fan. The power couple dated from 1999 to 2002.

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Hilary Duff & Aaron Carter

You know you were SO JEALOUS of Lizzie McGuire when she got smooched by Carter on set of his Christmas music video. According to Carter, the two started dating when Carter was only 13 years old, in 2000. They dated on and off for a year and a half before Carter ditched Duff for Lindsay Lohan — ouch! It looks like Duff got the last laugh, because Carter still wants this relationship to be a thing, as does the middle schooler in all of us.

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Vanessa Hudgens & Zac Efron

The Disney co-stars were adorable together. They allegedly began dating in 2005, after meeting on the set of High School Musical, in which they played love interests Gabriella and Troy. Here’s the evidence that proves they’re insanely cute together.

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Ben Affleck & Jennifer Lopez

Sure, Bennifer was cute together, but more than that, their relationship was a huge media frenzy from the time they began dating in 2002 to 2004, when they split. For whatever reason, Bennifer was a very, very big deal, and it was fun reading about the juicy drama.

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Adam Brody & Rachel Bilson

Who didn’t love Seth and Summer? The two dated from 2004 to 2007 after meeting on the set of The O.C. and even adopted a puppy together. Though both Brody and Bilson are happy in their respective relationships, I secretly wish that these two could have made it work, if only selfishly because of their O.C. counterparts.

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Penn Badgley & Blake Lively

By the end of Gossip Girl’s run, I didn’t know how to feel about Dan Humphrey. I did, however, secretly wish that Dan and Serena were equally as perfect for one another offscreen. Badgley and Lively broke up in 2010 after over 3 years together — and two years before their characters ended their time on Gossip Girl as a married couple!

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Nick Lachey & Jessica Simpson

Newleyweds stars Lachey and Simpson asked existential questions like whether “Chicken of the Sea” was fish or poultry but divorced in 2006 after four years of marriage.

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Hilary Duff & Joel Madden

The pop princess and the punk dated for over two years from 2003 to 2006, during which time they were downright adorable. Duff even referred to Madden as the “most respectful boyfriend” she has ever had.

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Lauren Conrad & Brody Jenner

According to Jenner himself, him and Conrad (his cuddle buddy on The Hills) were never a real couple. I refuse to believe that as it means my entire life up to this point has been a lie.

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Jessica Szohr & Ed Westwick

This Gossip Girl couple has been on and off since 2008 but somehow always manages to look ever-so coupley together when snapped by the paparazzi.

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Liam Hemsworth & Miley Cyrus

I never thought much about this couple until I read about how these two only have nice things to say about the other. Why couldn’t you two kids work it out?!?

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Sophia Bush & Austin Nichols

Bush was married to One Tree Hil l co-star Chad Michael Murray, but her later-seasons beau Nichols proved to be a much better fit… mainly because he didn’t allegedly cheat on her. Nichols and Bush dated on and off from 2006 to 2012 before splitting up.

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Nina Dobrev & Ian Somerhalder

Elena and Damon forever, right? These two Vampire Diaries co-stars dated from 2010 to 2013, and are keeping things friendly on set. Still, the lustful looks between Damon and Elena can’t be chocked up to acting alone… right?

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Nicholas Holt & Jennifer Lawrence

The X-Men: Days of Futures Past co-stars seemed like the nerdy-cool couple you’d go drink cheap beer and play Jenga with. They dated on-and-off from 2011 to 2014.

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Brad Pitt & Jennifer Aniston

I know, I know — get over it, right? And I am. I mean, Pitt just married Angelina Jolie, his partner since 2005 — I think that’s a sign that Pitt and Aniston are done for good. At the same time, photos like the one above make me quite nostalgic for the days where this couple ruled the red carpet.

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Ryan Gosling & Rachel McAdams

The stars of The Notebook dated from 2004 to 2007, and though they have both moved on, we’ll never not want Noah and Allie to get back together.

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Orlando Bloom & Miranda Kerr

The most recent celebrity breakup on this list (they officially broke things off in March 2013) I was really rooting for these two. Unfortunately, like every other couple on this list, it just wasn’t meant to be — despite how beautiful of a couple they make.

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