Life

10 Celebrity Relationships That Defined The Decade

The hookups, engagements, splits, and weird couplings we couldn't get enough of.

Love is complicated. It can be brutal and paralyzing and deeply confusing, and not even the richest and most beautiful and most deeply privileged people in the world can navigate it cleanly and gracefully all the time.

So while we’re going through our list of the celebrity couples who people couldn’t stop obsessing over this decade, and what we might be able to learn from those relationships, we’re also acknowledging that these are real people with real emotions. Yes, even Chad Kroeger.

Kristen Stewart and Robert Pattinson

Kristen Stewart and Robert Pattinson promote "The Twilight Saga: Breaking Dawn - Part 2" in Madrid in 2012.
Kristen Stewart and Robert Pattinson promote "The Twilight Saga: Breaking Dawn - Part 2" in Madrid in 2012.

The timeline: The actors started dating in 2009 and broke up in 2012, after she was spotted kissing married director Rupert Sanders. Stewart and Pattinson briefly got back together in 2013 before splitting for good.

Their current status? Broken up, but on decent terms.

The story: Doesn’t this feel like it happened a lifetime ago? The K-Stew/R-Pattz saga, beloved by “Twilight” tweens and tabloids alike, was all anyone could talk about in the early 2010.

While the breakup was dramatic at the time, the two seem to be in a good place now. In an interview with Howard Stern in November, Stewart talked about how he was her “first love” and said she would have married him, if given the chance.

Stewart has said she doesn’t want to label her sexuality, but since their split, she has mostly dated women, and is currently in a relationship with screenwriter Dylan Meyer.

Pattinson ended an engagement with musician FKA Twigs in 2017.

The lesson: The first person you date — or love — is rarely the person you end up with, and that’s OK.

Neil Patrick Harris and David Burtka

Neil Patrick Harris, left, with husband David Burtka at the South Beach Wine & Food Festival in Miami in February.
Neil Patrick Harris, left, with husband David Burtka at the South Beach Wine & Food Festival in Miami in February.

The timeline: They’ve been together since 2004, and got married in 2014.

Their current status? Still married, with twins.

The story: The actors got engaged in 2006 — but didn’t make it “official” until same-sex marriage became legal in New York five years later.

“We’ve been wearing engagement rings for ages, waiting for an available date,” Harris wrote on Twitter in 2011, after the announcement.

The lesson: Social progress is slow and hard, but the bigots won’t win.

The other lesson: The family that Halloweens together, stays together.

Katie Holmes and Tom Cruise

The timeline: The actors got engaged in 2005, seven weeks after they met, shortly following his couch-jumping on “Oprah.” They married in 2006.

Their current status? Divorced, with one child together.

Tom Cruise and Katie Holmes at the Vanity Fair Oscar Party in February 2012. They divorced by the end of the year.
Tom Cruise and Katie Holmes at the Vanity Fair Oscar Party in February 2012. They divorced by the end of the year.

The story: While it’s possible they were really in love and then split up for normal reasons, multiple sources allege that it’s way more possible that it was a creepy arrangement orchestrated by an oppressive cult.

The lesson: Don’t get into Scientology, ever.

Brad Pitt and Angelina Jolie

Angelina Jolie and Brad Pitt at the premiere of "By the Sea" in 2015.
Angelina Jolie and Brad Pitt at the premiere of "By the Sea" in 2015.

The timeline: They got together in 2005, had their first child in 2006, married in 2014, and divorced in 2016.

Their current status? Divorced, with six children together.

The story: We really thought this one would last forever.

The lesson: Heartbreak is an inevitability. It happened to Jolie, one of the most beautiful women in the world. It happened to Pitt, who said their breakup made him cry the first time in 20 years.

Runners-up: Some other couples we thought would stay together forever, but who split up this decade, include:

Watch: Celebrity breakups of 2019. Story continues after video.

Chrissy Teigen and John Legend

The timeline: The model/TV personality and the Emmy, Grammy, Oscar, Tony Award-winning musician started dating in 2007, got engaged in 2011, were married in 2013, and had their first child in 2016.

Their current status? Married with two kids.

John Legend and Chrissy Teigen at the 2019 Baby2Baby gala in November.
John Legend and Chrissy Teigen at the 2019 Baby2Baby gala in November.

The story: They’re sharp, funny, candid about their lives and super supportive of one another. It’s hard not to fall in love with them.

The lesson: Kind and handsome men really earn their sexy status when they pair up with women who are opinionated and smart.

Runners-up: Some other couples holding it together in a way that’s inspiring include Will Smith and Jada Pinkett Smith, PK Subban and Lindsey Vonn, Prince Harry and Meghan Markle, and J.Lo and A-Rod.

Ariana Grande and Pete Davidson

Pete Davidson and Ariana Grande at the 2018 MTV Video Music Awards.
Pete Davidson and Ariana Grande at the 2018 MTV Video Music Awards.

The timeline: The “Saturday Night Live” comedian and the award-winning singer started dating in May 2018, were engaged by June, and split up in October.

Their current status? Very much not together.

The story: It was the best of times, it was the worst of times. They got engaged a few weeks after they started dating!!

The lesson: Passion is wonderful, and it’s great to be excited about a new relationship. But you have your whole life to get married! For every “my mom and dad got engaged after two weeks and they’re still together” story, I can give you a dozen more sad breakups.

Essentially, I’m your judgey friend telling you that if you’re still measuring how many weeks you’ve been together, you probably shouldn’t get engaged yet.

Runners-up: Others in the quickie engagement category include:

Avril Lavigne and Chad Kroeger

Chad Kroeger and Avril Lavigne on the red carpet at the 2013 MuchMusic Video Awards.
Chad Kroeger and Avril Lavigne on the red carpet at the 2013 MuchMusic Video Awards.

The timeline: The musicians started dating in 2012, and surprised everyone when they got married on Canada Day 2013. They split two years later.

Their current status? Divorced, but still “very close.”

The story: Sometimes love is truly baffling. Sometimes it makes entirely no sense. And sometimes we just have to choice but to honour that.

The lesson: Is there a lesson here, really? The closest we can approximate here is: sometimes love is just plain weird, and there’s really nothing we can do about that.

Runners-up: Other couples that had us making 🤔this face 🤔 include:

George and Amal Clooney

Amal Clooney and George Clooney at the series premiere of "Catch 22" in London.
Amal Clooney and George Clooney at the series premiere of "Catch 22" in London.

The timeline: They met in 2013, married in 2014, and had children in 2017.

Their current status? Married with twins.

The story: After decades of being an incorrigible bachelor who dated reality stars and wrestlers, actor Clooney finally settled down with a human rights lawyer.

The lesson: Unless they’re literally George Clooney, no one actually goes from being a player to being a stand-up guy. Don’t expect this kind of behaviour from regular people.

Meghan Duggan and Gillian Apps

Meghan Duggan and Gillian Apps
Meghan Duggan and Gillian Apps

The timeline: We don’t know how long they’ve been a couple, but the two hockey champs have faced off at the Olympics in 2010 and 2014. (Apps’ Team Canada came first, natch, with Duggan’s Team USA a close second.) They married in September 2018.

Their current status? Married, with a baby on the way.

The story: Why isn’t there a biopic yet?! Rivals who fall in love is such a good story!

The lesson: Love can overcome (almost) any obstacle.

Runners-up: Caroline Ouellette and Julie Chu, also a Canada-US women’s hockey rivalry-turned-romance, who welcomed a baby girl in 2017. Also, Tessa Virtue and Scott Moir, who are not a couple, but are also more of a couple than many actual couples, if you catch our drift.

Serena Williams and Alexis Ohanian

Serena Williams and Alexis Ohanian at the 2018 Brand Genius Awards in New York.
Serena Williams and Alexis Ohanian at the 2018 Brand Genius Awards in New York.

The timeline: They met in Rome in 2015 and got in 2016. In 2017 they had a baby, who was a part of their wedding two months later.

Their current status? Married, with a very cute daughter.

The story: Ohanian, the co-founder of Reddit, is endlessly supportive of his tennis superstar wife. Instead of feeling threatened by her colossal success, he celebrates her at every turn, regularly showing up to cheer her on and encouraging other dads to be equitable parents by working to destroy the stigma around paternity leave.

He even subtly jabbed at her competition by showing up to a match where Williams was playing Maria Sharapova, who tested positive for performance-enhancing drugs in 2016, wearing an anti-drugs shirt. Classic.

The lesson: Do things on your own schedule — there’s no reason to get married before having kids, if that’s what works for you. And, obviously, find you someone who’s willing to take on your feuds, because that’s true love.

Runners-up: Kurt Russell and Goldie Hawn, who have been together nearly 40 years without getting married. Also, Elizabeth May and John Kidder for proving that romance is not the exclusive domain of 22-year-olds, no matter what many tabloids would have you believe.