These 15 Celeb Couples Broke Up & Still Had To Work Together, So That's Awk

Y'all, I can barely keep up with this on-again, off-again relationship. If you recall, dating rumors began swirling around the real-life Jughead and Betty in 2017 and reportedly called it quits in July 2019. The brutal part was that their reported split happened before they had to appear at Comic-Con together, and they were still filming season 4 of Riverdale. Rest assured that Cole Sprouse and Lili Reinhart have since resumed their relationship, though, and are still very much together as of April 20 (despite the rumors that Sprouse was cheating with Kaia Gerber). Quit playing games with my heart, Bughead.

Mindy Kaling and B.J. Novak's real-life romance was the stuff of rom-coms: They grew up 10 minutes away from each other, but never met until they worked together as writers and actors on The Office.

While their exact relationship timeline is a bit unclear, from what they've divulged, it seem that their dating experience mimics that of their on-again, off-again characters, Kelly and Ryan. The only difference? These two became BFFs after their romance fizzled out. In fact, the exes not only kept things professional on the Dunder Mifflin set, but collaborated on other shows (The Mindy Project), worked on books together, and have been seen arm-in-arm on many red carpets. Kaling even named Novak as the godfather of her daughter Katherine, who was born in December 2017. I'm not crying, you are.

Even after Drake and Rihanna's relationship came to an end, they made multiple hits together. The power couple was first romantically linked in 2009 and continued clearly flirting while insisting they were "just friends" over the next year. Drake confirmed in a New York Times interview that their relationship had fizzled out (and he wasn't thrilled with how it went down). Then, in October 2010, the duo released their steamy music video for "What's My Name?" — sending fans and stans into a serious frenzy. They continued working together throughout the 2010s — like on "Take Care" in 2011 and "Work" in 2016. Their music video chemistry never re-ignited the flame IRL, however. In a 2018 interview with Vogue, Bad Girl RiRi said of Drizzy: "We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Kourt Kardashian and Scott Disick are basically pros at working together after breaking up — after all, they've done it for years on the reality show Keeping Up With the Kardashians. Since calling it quits for good in 2015 (after nine years together), they've continued co-parenting Mason, Penelope, and Reign while also documenting their lives on the hit reality series together — which means fans have been along for the wild rollercoaster ride every step of the way.

Speaking of Kardashian couples, Khloé has been through a lot with Tristan Thompson over the years, but that hasn't stopped them from appearing on KUWTK together. Remember when Thompson was accused of cheating back in 2018 just days before she gave birth to their daughter, True? The couple stuck it out, but less than a year later, another cheating scandal emerged — this time, with Kylie Jenner's best friend, Jordyn Woods. Khloe ending her relationship with Tristan for good, but they've continued to share tidbits from their lives on multiple episodes of her fam's reality show. In one August 2019 episode, Kardashian invites her ex to their daughter's first birthday party (resulting in some drama), and recent episodes have focused on the challenges of co-parenting.

Even though Damon and Elena were obv #endgame, Ian Somerhalder and Nina Dobrev were not. After dating for three years, the off-screen couple split up in 2013 — but since Dobrev didn’t leave The Vampire Diaries until 2015, that means they had to share many *intimate* on-screen moments together for literal years after their relationship was over. It couldn’t have been that awk, however, because the duo still managed to snag the "Best Chemistry" trophy at the 2014 People’s Choice Awards for their steamy scenes. It even seems like Dobrev has remained friends with Somerhalder, as well as his now-wife, Nikki Reed.

Twilight fans were nothing short of thrilled when the actors playing Bella and Edward fell in love. While their chemistry on screen was explosive, it definitely wasn’t smooth sailing for the couple IRL, though. They split for the first time in 2012, briefly reunited, and then parted ways for good in 2013. The timing of their first breakup was tough because they still had to do months of press together to promote the Twilight series’ final film. Fortunately, it seems like there’s no bad blood between the actors — in fact, they’ve even been seen casually hanging out in recent years.

Cameron Diaz is enjoying marital bliss with Benji Madden, and Justin Timberlake has been happily married to Jessica Biel for eight years now. But once upon a time, between 2003 and 2007, Diaz and Timberlake were an item. Years after they split and moved on in their dating lives, however, they joined forces to star in the comedy film Bad Teacher — in which they actually had a love scene. Their co-star Lucy Punch said that surprisingly, that wasn't as awkward as it sounds.

"I go on set and I'm like, 'Oh, they're just great friends, it turns out [and] really mature and adult. How boring!'" the actress told MTV at the premiere.

I wish I could tell you that like Seth and Summer, the actors playing them lived happily ever after, but unfortunately, they ended their relationship in 2006. As fate would have it, that was right before they had to film their characters' future wedding on The O.C. Apparently, it was a pretty amicable split, because Rachel Bilson and Adam Brody managed to continue working together until the show ended in 2007. Back in 2014, Brody did a Reddit AMA in which a fan asked him about Bilson and he called her "one of the greats" — talk about #ExGoals.

Gilmore Girls fans, prepare to have your mind blown — because Alexis Bledel and Milo Ventimiglia weren't just on-screen love interests, they also had a romance in real life that lasted for four years. Just like their characters, they split up in 2006. However, that wasn't the end of their working relationship. They later reunited for the Netflix reboot, Gilmore Girls: A Year in the Life.

Fun fact: Ventimiglia also dated his Heroes costar Hayden Panettiere, and had to keep working alongside her on set for the final season after they broke up. So, yeah, he's kind of a pro at this.

Hey, Upper East Siders: ICYMI, Lonely Boy and Serena van der Woodsen had such a strong spark on Gossip Girl that they started up a relationship off-screen. Their romance lasted for about three years, but they broke up before they finished filming the final season of the show. That means that they were already exes by the time Dan and Serena got married in the finale (woof). Props to them, though, because their professional relationship on set definitely didn't suffer (and their on-screen romance remained as convincing as ever). During a 2015 appearance on Watch What Happens Live, Badgley actually revealed that Lively was both his best and worst on-screen kiss — which makes total sense.

Lively and Badgley's relationship wasn't the only one that started on the GG set. Jessica Szohr and Ed Westwick also took a cue from their characters Vanessa and Chuck, and dated on and off between 2008 and 2012. While they broke up for the first time in 2010, Gossip Girl didn't end until 2012.

Following in Reinhart and Sprouse's footsteps, Camila Mendes and Charles Melton emerged as Riverdale's second couple in 2018 (when they made it Instagram official). Sadly, after celebrating their one-year anniversary together, Veggie announced that they were stepping away from the relationship. They still had to film the show's fourth season together, though.

Lily Collins and Taylor Lautner's short-lived romance started while they were co-starring in Abduction together in 2010 — but it didn't last until opening weekend. Since they split before the premiere, they still had to unite for a lengthy press tour ahead of the premiere.

I'm still not over Jenny Slate and Chris Evans' 2018 breakup, TBQH, but there is still a happy ending to their relationship. The actors met on the set of Gifted, and fell in love for real, just like their characters did in the film. Since they split before the movie officially premiered, they had to continue working together to promote it.

If you needed any proof of the fact that they're literally Exes Of The Year, after they broke up for the first time in 2017, Evans called Slate "my favorite human," and Slate said Evans was "truly one of the kindest people" she's ever met. *Sigh* — yep, still not over it.