Love Hurts: The Worst Celebrity Valentine's Day Breakups Exposed
Feb. 18 2020, Updated 5:08 p.m. ET
Lovers usually look forward to Valentine's Day, but for a group of celebrities, this Friday, February 14, will bring back bad memories of their breakups on or around the day celebrating romance.
Although Jennifer Aniston and Justin Theroux actually parted at the end of 2017, they bizarrely chose to announce their split on February 16, 2018, just two days after the holiday.
The two, who married in 2015, stunned fans by issuing a joint statement that said, "We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."
Unlucky in love Aniston was previously married to Brad Pitt for five years.
She's not the only one to have an unromantic time during what's traditionally the month of love. Hilary Duff and first husband Mike Comrie filed for divorce near Valentine's Day in 2015 and finalized their divorce the following February.
Khloe Kardashian split from baby daddy Tristan Thompson just before Valentine's Day last year after catching two-timing Tristan cheating on her with little sister Kylie Jenner’s lifelong BFF Jordyn Woods.
As RadarOnline.com readers know, Tristan cheated on Khloe the first time when she was about to give birth to their daughter True.
The Keeping Up with the Kardashians star took him back, but then he betrayed her again, with Jordyn, who admitted she kissed Tristan at his house party.
Lady Gaga also had a bummer of a Valentine's Day last year. Just days after she attended the 2019 Grammy Awards by herself on Feb. 10, the news broke that the "Bad Romance" singer had split from agent fiancé Christian Carino.
Young love didn't work for Hayden Panettiere, who reportedly ended her romance which started at age 18 with her Heroes co-star Milo Ventimiglia just a few days after Valentine's Day 2009. She also got into an altercation with boyfriend Brian Hickerson on Valentine's Day 2020.
Scroll through RadarOnline.com's gallery for more.
Hayden Panettiere & Brian Hickerson
Hayden Panettiere’s bad news boyfriend, Brian Hickerson, is accused of hitting the actress on Valentine’s day. Detective Clayton Platt told RadarOnline.com in an exclusive statement that “he was arrested on February 14 and charged with domestic battery.” He’s since been released.
Hickerson allegedly got in a fight with Panettiere while intoxicated and struck her with a closed fist at around 2:30 a.m. while the two were vacationing in Wyoming.
Jennifer Aniston And Justin Theroux
The couple announced just after Valentine's Day 2018 that they were calling it quits. The actor has said "it was kind of the most gentle separation, in that there was no animosity."
Jennifer Lopez And Sean “P. Diddy” Combs
The Super Bowl halftime show queen is now engaged to former Yankees star Alex Rodriguez, but years ago, JLo had a torrid romance with the rapper and they attended the Grammys together. Combs' rep announced their split on Valentine's Day, 2001.
Khloe Kardashian And Tristan Thompson
Sources told RadarOnline.com that the reality TV star and her basketball hunk baby daddy split just before Valentine's Day last year. The next month, Khloe told fans Tristan's cheating had caused "a rollercoaster of emotions."
Amanda Seyfried And Ryan Phillippe
The actors dated for a few months in late 2010 and split in early February 2011. They reconciled that March, but later split for good.
Malcolm-Jamal Warner And Regina King
The actress talked about a famous ex most assumed was Warner, telling Us Weekly that she'd once been dumped on Valentine's Day 2013. "Someone broke up with me on Valentine's Day," she said, "Then he actually sent me flowers that said, 'I still love you' and I threw the flowers in the trash."
Jude Law And Sienna Miller
he week before Valentine's Day in 2011, the passionate twosome finally ended their fraught relationship. Five years earlier, Jude had been caught in an alleged cheating scandal with his family's nanny. Incredibly, he and Miller stayed together but later ended things around the holiday.
Nina Dobrev And Austin Stowell
The Vampire Diaries beauty and her actor boyfriend's split news broke a few days before Valentine's Day 2016. On the holiday itsef, Dobrev posted a photo with her friends and captioned it, "Sunday Funday #HappyGALentinesDay."
Lady Gaga And Christian Carino
The singer got engaged to Carino during her A Star Is Born heyday, but they split in February 2019 after two years together.
Hilary Duff And Mike Comrie
The star and hockey player husband, the father of her son Luca, were embroiled in divorce around Valentine's Day 2015. It was finalized in a year and Duff went on to wed Matthew Koma last December, just days before Christmas!
Jordin Sparks And Sage The Gemini
The musicians dated for nine months and announced their split four days before Valentine's in 2016.
Hayden Panettiere And Milo Ventimiglia
The Heroes stars dated when she was just 18 and he was 30. But right after the heart holiday in 2009, they were done after two years together.
Maci Bookout And Kyle King
The Teen Mom broke up with boyfriend Kyle King the week before Valentine's Day in 2012 amid rumors he'd cheated. The young couple reconciled before splitting up again for good.
Diana Agron And Alex Pettyfer
The Glee blonde appeared in "I Am Number Four" with actor Alex Pettyfer and the two fell in love. However, they went through a nasty bustup in February 2011. She reportedly moved out of their home close to Valentine's Day.
Sophia Bush And Austin Nichols
The One Tree Hill co-stars made a cute couple but when they finally separated after six years in 2012, it was announced right after Valentine's Day. A source told Us Weekly, which first reported the split, that "she didn't think he was the one" and was "moving on."