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The Messiest Celebrity Romantic Affairs Over the Years (Update)

As Valentine Day nears, remember love can also be messy. So let's look at the affairs that had everyone talking .

Photo: Getty Images Dia Dipasupil

Ever since Good Morning America anchors TJ Holmes and Amy Robach were caught having an affair, they have been the talk of social media. Recently rumors spread they were out of the job, but photos show they remained hot and heavy. With this scandal still in the news and Valentineโ€™s Day right around the corner, The Root decided to take a look back at some of the messiest celebrity romantic affairs over the years.

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Trump’s Tariffs Might Stick Around. What Should We Buy Now?
Trump’s Tariffs Might Stick Around. What Should We Buy Now?

TJ Holmes & Amy Robach

Photo: Getty Images Paula Lobo/ABC

Obviously, we had to start with the most recent scandal. The two GMA anchors always had amazing chemistry while on live television. But many had no idea it would turn into a romantic affair between the two. ABC is investigating Holmes for his relationship with Roback and potentially other colleagues.

Ime Udoka & Nia Long

Photo: Getty Images Randy Shropshire/WireImage

This scandal shocked the entertainment and sports world. In September, Ime Udoka, head coach of the Boston Celtics, was suspended for a year for having a consensual relationship with a woman who is a part of the Celticsโ€™ staff. This ultimately led to Nia Long and Udoka splitting after a 13-year relationship.

Jada Smith & August Alsina

Photo: Getty Images Paras Griffin

How could we forget the โ€œEntanglementโ€ that was Jada Smith and August Alsina? During a random sit-down with Angela Yee, August Alsina claimed that he had an intimate relationship with Will Smithโ€™s wife, Jada Pinkett Smith. Will and Jada eventually addressed the relationship during an infamous episode of Red Table Talk and explained that the two were separated when Jada was with August.

Tristan Thompson & Khloe Kardashian

Photo: Getty Images Jerritt Clark

I donโ€™t even have enough fingers on my hands to count the number of times Tristan Thompson has allegedly cheated on his longtime girlfriend Khloe Kardashian. The most infamous incident was when he cheated on Khloe with Kylie Jennerโ€™s longtime friend, Jordyn Woods. During an episode of Red Table Talk, Jordyn revealed that Tristan kissed her. This essentially ended her friendship with Kylie and the positive relationship she had with the Kardashians.

Tiger Woods & Elin Nordegren

Photo: Getty Images David Cannon

Tiger and Elin were married from 2004 to 2010. What ultimately led to them divorcing was that Tiger reportedly confessed to sleeping with 120 other women while the two were married.

Jay-Z & โ€œBecky With the Good Hairโ€ย 

Photo: Getty Images Mike Coppola

In 2013, rumors came out that the legendary Brooklyn rapper cheated on Beyoncรฉ. Those rumors gained some validity when Beyโ€™s sister, Solange, went at Jay during the infamous elevator incident. On Beyonceโ€™s classic 2016 album, Lemonade, she made multiple references that she was being cheated on. On Jay-Zโ€™s 2017 album, 4:44, Jay-Z seemingly admits to cheating on his wife with โ€œBecky with the good hair.โ€

Wendy Williams & Kevin Hunter

Photo: Getty Images John Lamparski/WireImage

After being married for over two decades, Wendy Williams filed for divorce from her husband Kevin Hunter amid rumors that he had been cheating with a woman who gave birth to a baby in 2019. Wendy later revealed that Hunter was a โ€œserialโ€ cheater while they were married.

Cicely Tyson & Miles Davis

Photo: Getty Images Robin Platzer/IMAGES

The legendary entertainers were married from 1981 to 1988. Allegedly, Cicely Tyson lost her cool oftentimes and they were multiple rumors that Miles Davis cheated on her while they were together.

Marvin Gaye & Janis Hunter Gaye

Photo: Getty Images Michael Ochs Archives

Marvin Gayeโ€™s second wife, Janis Hunter Gaye, allegedly cheated on the legendary singer multiple times through the 1970s when they were married. In 2015, Jan released a book, After the Dance: My Life With Marvin Gaye, where she admitted to having an affair with R&B singers Frankie Beverly and Teddy Pendergrass. Janis died on Dec. 3 at the age of 66.

Dwayne Wade & Gabrielle Union

Photo: Getty Images Edward Berthelot

Dwayne Wade has been pretty open about his infidelity issues. He cheated on his childhood sweetheart, Siohvaughn Funches-Wade, with Gabrielle Union. Then, years later, he turned around and cheated on Union and had a baby with another woman.

Usher & Tameka

https://www.youtube.com/watch?v=jCkRW6aAXDs

On an episode of Oprahโ€™s Next Chapter, Usher admitted to being unfaithful during his marriage with his ex-wife, Tameka Foster.

Kobe Bryant & Vanessa Bryant

Photo: Getty Images Kirby Lee/WireImage

When Kobe Bryant cheated on his wife, it almost landed him in prison. During an infamous press conference with Vanessa, he denied having raped the woman who accused him of the crime but did admit to having an adulterous relationship with her.

Alicia Keys & Swizz Beat

Photo: Getty Images Jason Mendez

Before Swizz Beatz had a loving relationship with Alicia Keys, he was married to Mashonda, a successful singer and songwriter in her own right. While the three are now friends, Mashonda accused Swizz of cheating on Alicia while they were married.

Carmelo Anthony & Lala Anthony

Photo: Getty Images Shareif Ziyadat

The star basketball player and successful entertainer dated since 2004. LaLa decided to split with the NBA All-Star in 2017 after he was accused of cheating and having a baby with another woman. In June 2021, LaLa filed for divorce.

Lionel Ritchie & Brenda Harvey

Photo: Getty Images Ron Wolfson/Michael Ochs Archive

Allegedly, Ritchie was caught cheating on his first wife, Brenda Harvey, with Diane Alexander, who ended up being his second wife. Reportedly, Harvey beat the crap out of Ritchie and Alexander when she caught them sleeping together. The encounter was hilariously described in an episode of The Boondocks.

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