What Jennifer Love Hewitt's Exes Really Said About Her

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The road to "happily ever after" is often littered with the skeletons of past loves, and no one knows that better than Jennifer Love Hewitt. After working as a child actor on the Disney Channel's "Kids Incorporated," her breakthrough role came in the weepy Fox teen drama "Party of Five." From there, the actor became a sex symbol who made regular appearances in men's magazines like "Maxim." Hewitt parlayed her popularity into becoming an official '90s scream queen with "I Still Know What You Did Last Summer" and its sequels. From there, she continued to rule the small screen with hits like "The Ghost Whisperer," "The Client List," and "9-1-1."

As if she wasn't busy enough with her decades-spanning career, she's also had a rather eventful personal life. Hewitt, who once told Entertainment Tonight that she sees herself as a "hopeless romantic," was linked to a number of fellow A-listers before finally finding the man who would become her husband. In 2013, Hewitt tied the knot with "The Client" co-star Brian Hallisay, and they went on to have three kids together. 

Before the "Party of Five" star settled down, she took a long and hard look at her own rocky dating life and turned it into a memoir. In 2010, she released "The Day I Shot Cupid: Hello, My Name Is Jennifer Love Hewitt and I'm a Love-aholic," a book that offers up a lot of relatable and humorous dating advice. But who were the men who made Hewitt a "love-aholic" and led her down the broken road of failed relationships before she found true love? And what did her exes have to say about dating the late '90s/early '00s it girl? Here's what Hewitt's former significant others and rumored romances have dished over the years.

Pop-rap boy band LFO (Lyte Funkie Ones) formed in the mid-'90s out of Massachusetts. One of the trio's biggest hits, "Summer Girls," was released in 1999 as their first single. It climbed up the charts to become one of the decade's biggest summertime anthems. The second single, "Girl On TV," certainly wasn't as big of a hit, but its backstory is as juicy as can be.

The band's frontman, Rich Cronin, said he penned "Girl On TV" about his late-century fling with Jennifer Love Hewitt. It turns out that Cronin's brief affair with the actor went from piping hot to ice cold in the blink of an eye. "It went from 'I love you' every day to, literally, within a week, 'I hate you, don't ever call me again,'" Cronin told SFGATE in 2001.

According to Cronin, the last time he spoke with Hewitt, she told him, "I've got to go. You've hurt me too much. I don't want you to make me upset again." Cronin added that he tried to contact her after things ended, but Hewitt did not return his calls. Hewitt's abrupt stop to the relationship left Cronin with more questions than answers. "Every day I hear about it. I've got to think, 'What the hell happened?' We were really close," he lamented. Cronin passed away in 2010 from leukemia. He was 36 years old. 

John Mayer has repeatedly tried to set the record straight about his hit song "Your Body Is a Wonderland," insisting that, contrary to popular belief, the 2001 smash is not about his former girlfriend Jennifer Love Hewitt. Mayer and Hewitt dated for about a year in 2002, and during their courtship, there was a lot of speculation about whether or not he penned that song for her.

According to Mayer, "Your Body Is a Wonderland" is actually about a girl he dated in high school. "That was about my first girlfriend," Mayer said on the "Call Her Daddy" podcast. "That was about the feeling, which I think was already sort of nostalgic. I was 21 when I wrote that song and I was nostalgic for being 16." He also insisted that the song's lyrics existed way before he connected with Hewitt. "I had never met a celebrity when I wrote that song," he said. 

In a 2007 interview with Entertainment Weekly, Hewitt corroborated her ex's claim. "My body is far from a wonderland. My body is more like a pawnshop," she quipped. "There's a lot of interesting things put together, and if you look closely you'd probably be excited, but at first glance, not so much."

Carson Daly and Jennifer Love Hewitt were one of Hollywood's hottest couples at the turn-of-the-millennium. The MTV "Total Request Live" VJ and the small screen star dated for about a year in the late 90s. Before he married his wife, Siri Pinter, in 2005, Carson Daly had a long dating history that also included Tara Reid and Jaime Pressly.

According to Daly, he found out that his relationship with Hewitt was kaput from an unexpected source. "I woke up to Howard Stern telling me my relationship with [Jennifer] was over. Then I heard Steve Kmetko on E! say, 'Just off the Associated Press: Jennifer Love Hewitt and Carson Daly have officially broken up,'" Carson told People in 2000 (via E! News).

Daly added that he confronted Hewitt about the surprise press release. He said that he told his now-ex, "If we were going to break up officially like this, maybe we could have just talked about it. I don't see why you had to tell your publicist. And now I have been publicly humiliated."

Wilmer Valderrama had a no good very bad day on March 8, 2006. The "That '70s Show" star went on "The Howard Stern Show" and proceeded to give way too much personal information on his dating life. Say what you will about The King of All Media, but he has an uncanny ability to make his guests feel so comfortable that they forget — or maybe don't care — that millions of people are listening. 

In one of the most ill-advised public relations moves ever, Valderrama openly dished the dirt on many of his alleged sexcapades with Hollywood starlets, including Mandy Moore and Lindsay Lohan. He also boasted that he had a fling with Hewitt, rating her an "8." 

Here's where things get even messier: While the two were rumored to be a thing in 1999 and 2000, Hewitt apparently disputed Valderrama's version of events. Per Fox News, she reportedly once said, "I was told that we had all these very steamy encounters and I was like, 'Really! Well, I would have loved to have been there.'" It's worth noting that Moore also disputed some of the comments Valderrama made about their relationship during his infamous "The Howard Stern Show" appearance.

Will Friedle and Jennifer Love Hewitt were an item when Hewitt made a guest appearance on the actor's hit TV show "Boy Meets World." In a meta moment, the show cast Hewitt to appear in the episode "And Then There Was Shawn," which served as a homage to her hit movie "I Know What You Did Last Summer." At one point, Friedle and Hewitt's characters make out in the hall of the school — and it's arguably 

On a 2024 episode of "Pod Meets World," the "Boy Meets World" rewatch podcast Friedle hosts with Danielle Fishel and Rider Strong, the series alumni didn't mince words about the kissing scene in "And Then There Was Shawn." Friedle acknowledged that it was pretty awkward to rewatch that part. "I don't remember it going that far. It was seriously, like, 'Wow, that's uncomfortable,'" said Friedle after watching the scene. "It was super intense. And I've had people even say to me, like, 'Oh, when I was a kid, I didn't realize you guys were together. So, it was just like, what the hell is going on?'" 

On a followup episode of "Pod Meets World," Friedle reflected on how great it was to work with his then-girlfriend in the episode. "Well she was game, and she was, you know, a great actress and would always throw herself into a project," he said.

Jennifer Love Hewitt and her "Ghost Whisperer" co-star Jamie Kennedy started dating in 2009. They started off as friends but got together romantically after Hewitt's engagement to Ross McCall ended. "I've heard about it — about being friends with somebody and it turns into something else and I've never really done that before and it's been great," Hewitt revealed on "The Ellen DeGeneres Show" (via NBC4 Washington). "He's hilarious and when you're with somebody funny they're always funny and it's just great."

It was also great for Kennedy, who could barely contain his exuberance when talking about his gal pal. "I'm in love!... It's like, 'Wow, you are hot," Kennedy told Ryan Seacrest on his radio show (via Irish Independent). "You can sing, you can dance, you're like, so smart and, wow, you can cook pasta fagioli, too.'"

They split up the following year in 2010. The timing of the breakup was unfortunate because it was announced while Hewitt was out doing publicity for her dating book, "The Day I Shot Cupid: My Name is Jennifer Love Hewitt and I'm a Love-Aholic." "It wasn't ideal timing," Hewitt acknowledged at the time, per CBS News. She then went on to quip, "Here's my relationship book and I'm single."

Winemaker Ben Flajnik is a Bachelor Nation double-dipper. He first appeared on Season 7 of "The Bachelorette," where he made it all the way to the top 2 before being denied the final rose. Ben was likable enough for ABC to bring him back to serve as the main man in Season 16 of "The Bachelor."

However, before he returned to the reality dating show world, Ben Flajnik went on a few dates with Jennifer Love Hewitt. The former Bachelor said that she contacted him because she wanted to come to his winery. "She's a nice girl, but I wasn't –- it was right in the middle of the time when I was deciding to be the 'Bachelor.' When this is all said and done, ending up with a Hollywood celebrity is not something that I want," he told USA Today.

Alas, Ben did not ultimately find true love on "The Bachelor." He proposed to contestant Courtney Robertson, but they broke up before getting to walk down the aisle. He did get married off-screen to Christina Flajnik in 2023.

Jennifer Love Hewitt almost had her happily ever after with Ross McCall. Hewitt met the Scottish actor in 2006 when he did a guest spot on her hit show "Ghost Whisperer." The couple dated for about two years and were engaged for another two years.

During a 2025 conversation on the podcast "Breaking Through with Ellina Abovian," McCall said that he first met Hewitt in his trailer while getting his makeup done for "Ghost Whisperer." It was a love-at-first-sight kind of moment. "We shook hands and said hello and that was it," said McCall. "Then we had this you know, monumental chemistry thing that rarely happens." McCall added they got "swept up in young love."

When Abovian asked the "Band of Brothers" star why their relationship fell apart, he replied, "So many things don't work out. I mean, we had a good go at it." He also told Abovian that if given another chance, he would have handled their time together differently. "[Y]ou know, with a certain level of maturity and understanding of now myself, number one, but also about relationships," he said.