became a household name in the ’90s, starring in dozens of TV shows and movies beginning in 1989. It’s no surprise that she quickly found love after landing in the spotlight. Jennifer Love Hewitt
Through the years, she was part of many A-list romances, dating
, Rich Cronin and Carson Daly among others. The John Mayer TRL host and the director dated in 1998 and did not hide their romance, walking the red carpet at her premiere of and later, I Know What You Did Last Summer at the MTV Video Music Awards.
After a year together, the pair split and he later claimed he found out via the news. In 2005, they reunited when she appeared on his talk show and even took a Cosmopolitan compatibility quiz, scoring a 92 percent. “Can we just say that, for the time being, no matter what happened, I was a really good girlfriend to you and you were a great boyfriend?” Hewitt asked. He responded, “The latter part is so true. The first part is definitely true.”
In 2018, the
Criminal Minds alum shared a throwback photo of the pair cozying up on the VMAs carpet. “In honor of the VMA red carpet tonight. This was my VMA moment. Someone said that hair was cute. We are no longer friends lol,” she captioned the Instagram photo. “Wow that was a long time ago. #throwback #vmaredcarpet #iFeelOldAF.”
That wasn’t the only notable romance in Hewitt’s life. She made headlines in 2002 after being spotted holding hands with Mayer. At the time, rumors surfaced that his song, “Your Body Is a Wonderland” was about her, but the song actually came out before the pair began dating and he later said that he wrote the song about his first love.
9-1-1 actor found The One years later, marrying her Client List costar Brian Hallisay in 2013. They welcomed daughter Autumn James in 2013 and son Atticus James in 2015.
Scroll through the gallery below for more of her dating history.
The actors, who both appeared on
Boy Meets World, were introduced by a friend and briefly dated in 1996. “Will takes good care of himself,” Hewitt shared at the time. “At the same time, he takes care of me.”
10 Things I Hate About You actor briefly dated Hewitt in 1997, when they costarred on Party of Five.
The TRL host and the
Can’t Hardly Wait actress dated in 1997, and attended many big red carpets together. He got her name tattooed on his leg. They split after one year and he reportedly found out the relationship was over when he heard the news on The Howard Stern Show. He buried the hatchet in 2005 when she came on Last Call With Carson Daly.
The actress was linked to the
That ‘70s Show star in 1999. During an interview on The Howard Stern Show in 2006, he was asked to rate her and gave her an 8 out of 10 in the bedroom. The actress later responded to the quotes, saying, “I was told, like, that we had all these very steamy encounters, and I was like, really? Well, I would have loved to have been there!”
The LFO singer dated the “How Do I Deal” singer from 1999 to 2000 after meeting backstage at the Blockbuster Entertainment Awards. She was the inspiration for the song “Girl on TV,” and she appeared in the music video. Cronin died in 2010 after battling leukemia.
After she appeared in Iglesias’ “Hero” music video in 2001, the duo had a brief romance.
Hewitt dated the Tony award nominee after she saw him in the Broadway production of
The Full Monty in 2001, but they split the next year.
The Golden Globe nominee and the “Half of My Heart” singer briefly dated in 2002. Their relationship was followed by rumors that his song, “Your Body Is a Wonderland,” is about her — something they both later denied. (He wrote the song before they dated.) In 2018, Hewitt called Mayer “one of the coolest people I ever met” during
Michael Rosenbaum’s “Inside of You” podcast.
Remember the Titans actor reportedly dated the Heartbreakers star in 2003.
In 2004, Hewitt was spotted with the
Blue Bloods actor.
Hewitt began dating her
Ghost Whisperer costar in 2005 and the pair got engaged in 2007. However, they split in December 2008.
In 2009, the
Tuxedo star briefly dated the Scream actor and dedicated her book, The Day I Shot Cupid, to him. They split in 2010.
Four months after her split from Kennedy, the
McKenna alum began dating the actor-director. Us confirmed their split in May 2011.
Hewitt first met Hallisay on
Love Bites in 2011. The pair reunited on The Client List the following year and tied the knot in 2013 after one year of dating. They share two children.
Courtesy Jennifer Love Hewitt/Instagram