Jake Gyllenhaal and Taylor Swift's brief but intense relationship reportedly inspired her album Red, especially the fan-favorite heartbreak anthem "All Too Well."Jennifer Lopez and Ben Affleck were the original "Bennifer" and dominated tabloids before calling off their 2003 wedding — only to rekindle the flame nearly 20 years later!Jason Alexander, Britney's childhood friend, married her on a whim in Las Vegas in 2004. The marriage was annulled almost immediately.Justin Timberlake had high-profile relationships with both Biel and Diaz before ultimately marrying Jessica Biel in 2012.Kim's flashy wedding to NBA player Kris Humphries was broadcast on reality TV, but their marriage crashed almost as fast as it aired.Julia Roberts called off her wedding to Kiefer Sutherland just days before the ceremony — and ran off to Ireland with his friend Jason Patric instead!Robert and Kristen's off-screen romance captured fans' hearts, but it fell apart after Kristen was caught cheating with a married director.Ethan Slater, Ariana's Wicked co-star, split from his wife shortly before going public with Ariana — prompting a lot of internet side-eyesKylie and Tyga's on-again-off-again relationship started when she was a teen and fueled years of tabloid drama.Jennifer Aniston's first marriage was to Brad Pitt in 2000 — and their split over Angelina Jolie sparked a media frenzy for years.Taylor Swift spilled the tea that Joe Jonas broke up with her in under 30 seconds — and then she wrote several savage songs about it.The Bachelorette's Tyler Cameron briefly dated both Gigi Hadid and later allegedly had a fling with Joe Alwyn's ex, making him a low-key gossip favorite.Brad and Angelina fell in love while filming Mr. & Mrs. Smith — despite him still being married to Jen — igniting one of Hollywood's most iconic love triangles.John Mayer's romantic history with both pop stars was one of the rumored sparks behind Taylor and Katy's long-standing (and very public) beef.Olivia Rodrigo's emotional hit was widely believed to be about Joshua Bassett and his relationship with Sabrina Carpenter, launching a Gen Z love triangle saga.Nicole Kidman was married to Tom Cruise for over a decade before they divorced in 2001. She later said she felt like a "child bride" during their marriage.Gwyneth Paltrow turned heads when she described her 2014 divorce from Coldplay's Chris Martin as a "conscious uncoupling," instantly becoming a meme.Ariana Grande and Pete Davidson got engaged after a whirlwind romance — but the fairy tale ended almost as fast as it began.Kristen Stewart was photographed kissing Rupert Sanders, her Snow White and the Huntsman director, while still dating Robert Pattinson — sparking major backlash.Gwyneth Paltrow dated both heartthrobs in the '90s, even getting engaged to Brad Pitt before they split in 1997.Zoë Kravitz and Channing Tatum sparked dating rumors when they arrived together at the 2021 Met Gala — and fans couldn't get enough of their chemistry.Chris Brown and Rihanna's tumultuous relationship turned violent in 2009, leading to public outrage and criminal charges.Olivia Wilde and Jason Sudeikis split just before she was seen with Harry Styles, sparking gossip and even rumors of drama on the Don't Worry Darling set.Jelena — Justin and Selena — were on and off for years, with drama, breakups, and reconciliation rumors constantly feeding the tabloids.Pamela and Tommy tied the knot in 1995 after just 96 hours of knowing each other. Their chaotic, passionate relationship became legendary — and scandalous.Tristan Thompson was caught kissing Jordyn Woods — Kylie Jenner's BFF at the time — while still with Khloé. Cue: Kardashian chaos.Britney Spears shocked fans by marrying Kevin Federline — and even more by documenting their chaotic life in the reality show Chaotic.Alia Shawkat sparked dating rumors with Brad Pitt and had past whispers with Justin Timberlake — though neither was ever officially confirmed.Kris Jenner split with Caitlyn Jenner (then Bruce) on the show, with cameras rolling during the emotional breakdown of their decades-long marriage.Taylor Swift's fans believe "All Too Well" (especially the scarf reference!) is about Jake Gyllenhaal, who allegedly ghosted her after their brief 2010 relationship.Wilmer Valderrama has a wild dating history, having dated Lindsay, Demi (who was 13 years older), and later her daughter, Rumer.Katy and Russell Brand had a whirlwind marriage that ended when he allegedly broke things off via text — ouch.Leo DiCaprio has a long list of model exes, and rumor has it he ended things with one of them by sending his assistant to deliver the message. Classic Leo.Tom Hiddleston had a fast-paced, paparazzi-fueled fling with Taylor in 2016. "Hiddleswift" was short-lived — but very public.Eddie Cibrian and LeAnn Rimes had a scandalous affair while filming a movie, leading to two divorces — and a storm of media fire.Ashton Kutcher played Kelso, Mila's ditzy boyfriend on That '70s Show. Years later, life imitated art when the two got married IRL.Rumor has it that Drake and J.Lo had a brief romance in 2017 — but he vanished just as fast as he slid into her DMs.Dennis Rodman and Madonna's wild, tabloid-fueled fling had everything: Vegas, handcuffs, and rumors of a baby proposal involving a private jet.Jennifer Aniston's real-life romance with Tate Donovan overlapped with Friends filming — and she married Brad Pitt shortly after (then… Jolie happened).Megan Fox met MGK on the set of Midnight in the Switchgrass and described it as instant "twin flame" energy. 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It's time to put your pop culture memory to the test. Let's see if you can earn your spot in the Gossip Hall of Fame. Ready to spill the tea?
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Who famously dated Taylor Swift and inspired multiple breakup songs?
Think you know your Hollywood hookups? From whirlwind flings to scandalous affairs and iconic power couples, the A-list dating pool is messier (and more entertaining) than a soap opera. But only true celebrity gossip gurus can keep track of who dated who - and when! Can you separate the PR stunts from the real heartbreaks? Do you remember who was caught kissing who at Coachella, or whose rebound made headlines? It's time to put your pop culture memory to the test. Let's see if you can earn your spot in the Gossip Hall of Fame. Ready to spill the tea?
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Think you know your Hollywood hookups? From whirlwind flings to scandalous affairs and iconic power couples, the A-list dating pool is messier (and more entertaining) than a soap opera. But only true celebrity gossip gurus can keep track of who dated who - and when! Can you separate the PR stunts from the real heartbreaks? Do you remember who was caught kissing who at Coachella, or whose rebound made headlines? It's time to put your pop culture memory to the test. Let's see if you can earn your spot in the Gossip Hall of Fame. Ready to spill the tea?